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1 72: If You Want to Grow—Stop Fixing the Wrong Problem 16:32
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LikedYou’re busy—but are you actually growing? In this episode, Nata Salvatori exposes a trap that’s costing service providers time, money, and sanity: chasing busywork that feels productive but doesn’t move the needle. She walks through a clear, five-step growth path—from clarifying your offer, validating through real sales, delivering sustainably, building repeatable systems, to scaling confidently. You’ll learn: How to spot and ditch “fake work” Why clarity beats complexity every time How to use real feedback to validate your offers Delivery tips that prevent burnout System creation that enables scaling How to honor your current phase of growth 📌 Ready to stop spinning your wheels and make real moves? Map your phase, pick your next action, and don’t be afraid to ask for help: 👉 accidentalceo.co/coaching Support the show…
Unlocking the Cheat Code for Go To Market with Justin Gray - Ep. 38
Manage episode 461466528 series 3556097
Content provided by Matt Amundson & Craig Rosenberg | Hosts of The Transaction, Craig Rosenberg, Matt Amundson | B2B Sales, and Marketing Experts - Hosts of The Transaction. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Matt Amundson & Craig Rosenberg | Hosts of The Transaction, Craig Rosenberg, Matt Amundson | B2B Sales, and Marketing Experts - Hosts of The Transaction or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://ppacc.player.fm/legal.
Justin Gray, author of the brand new The Go-to-Market Cheat Code and Co-Founder of In Revenue Capital joins Hosts Matt Amundson and Craig Rosenberg to share how to build more effective and efficient B2B partnership programs, why nothing seems to be working in marketing, and his cheat codes to go-to-market success in B2B. Justin explains how and why LeadMD evolved from being a competitor to building an extremely strong partnership with Marketo. There’s also a great discussion about what VCs and other investors look for in founders when investing in startups and how this has changed in recent history.
Also, Matt vehemently opposes accusations of being hyperbolic and Craig recants on one of his ill-concieved New Years resolutions.
Critical Takeaways
- The success of any partner progam depends first and foremost on executive alignment. Without buy-in from leadership, 99% of B2B partnerships will fail.
- No matter how good your content may be, you still have to earn the right and access to get your content in front of your target audience by building strong relationships.
- Stop looking for copy and paste playbooks to use that are being used by everyone else in the market. If you don’t you’ll just be adding your content and brand to the endless pile of lifeless, gray ooze of things that get ignored. Take a risk and you’ll at least have a chance of sticking out.
- Any partner motion begins with building a relationship with one person. Find the right people to focus on and start one at a time. This is a much quicker way to build real relationships and trust than trying to boil the ocean and make a play for everyone at once.
Sponsored Segment
Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/
Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com
Chapters
00:00 Introducing Justin Gray
00:50 The Origin Story of LeadMD and how they Partnered with Marketo
09:55 The Go-To-Market Cheat Code Book
16:47 Craig makes fun of Justin’s Office
18:12 Lessons on Relationships from The Wild West of the Payment Processing Industry
30:26 The Cycle of Innovation and Imitation
32:09 The Importance of Knowing Your Buyer
40:34 What Venture Capital looks for in Founders
46:50 Building Effective Partnerships
1:05:02 18th Book Plug of the Episode
Sign up for our Newsletter: https://thetransaction.substack.com/
Epic Quotes
- “ What's working is what has always worked which is trusted relationships” - Justin Gray
- “Innovators look for ideas” - Craig Rosenberg
Connect with Justin
- LinkedIn: https://www.linkedin.com/in/inrevenue/
- The Go-to-Market Cheat Code (Book): https://inrevenue.capital/cheat-code/
- Order The Go-to-Market Cheat Code on Amazon: https://amzn.to/4hjtrbA
- In Revenue Capital Website: https://inrevenue.capital/
- The GTM Cheat Code (Podcast): https://inrevenue.capital/insights/?article_category=podcast
Shoutouts
- Essentials/Fear of God Clothing: https://fearofgod.com/
- Focus
- MAAS Impact
- Chris Selland: https://www.linkedin.com/in/cselland/
- LeadMD
- Marketo
- Bill Binch: https://www.linkedin.com/in/bill-binch-302a4a2/
- Margaret Hoogerbeets: https://www.linkedin.com/in/mhoogerbeets/
- Amy Guarino: https://www.linkedin.com/in/amyguarino/
- Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/
- Scottsdale Princess: https://www.scottsdaleprincess.com/
- Josh Wagner: https://www.linkedin.com/in/joshwagneraz/
- Jon Miller: https://www.linkedin.com/in/jonmiller2/
- Jon Miller’s Post about the Tragedy of the Commons in Marketing: https://www.linkedin.com/posts/jonmiller2_mpb2b-b2bmarketing-marketingautomation-activity-7262460572032483328-hs0J?
- Dirty Money, Season 1, Episode 2: https://www.netflix.com/us/title/80118100?s=i&trkid=258593161&vlang=en
- Bessemer: https://www.bvp.com
- Nick Mehta: https://www.linkedin.com/in/nickmehta/
- Marc Beniof: https://www.linkedin.com/in/marcbenioff/
- Founder’s Fund: https://foundersfund.com/
- Asher Mathew: https://www.linkedin.com/in/ashermathew/
- AWS Marketplace: https://aws.amazon.com/marketplace
Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
64 episodes
ShareManage episode 461466528 series 3556097
Content provided by Matt Amundson & Craig Rosenberg | Hosts of The Transaction, Craig Rosenberg, Matt Amundson | B2B Sales, and Marketing Experts - Hosts of The Transaction. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Matt Amundson & Craig Rosenberg | Hosts of The Transaction, Craig Rosenberg, Matt Amundson | B2B Sales, and Marketing Experts - Hosts of The Transaction or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://ppacc.player.fm/legal.
Justin Gray, author of the brand new The Go-to-Market Cheat Code and Co-Founder of In Revenue Capital joins Hosts Matt Amundson and Craig Rosenberg to share how to build more effective and efficient B2B partnership programs, why nothing seems to be working in marketing, and his cheat codes to go-to-market success in B2B. Justin explains how and why LeadMD evolved from being a competitor to building an extremely strong partnership with Marketo. There’s also a great discussion about what VCs and other investors look for in founders when investing in startups and how this has changed in recent history.
Also, Matt vehemently opposes accusations of being hyperbolic and Craig recants on one of his ill-concieved New Years resolutions.
Critical Takeaways
- The success of any partner progam depends first and foremost on executive alignment. Without buy-in from leadership, 99% of B2B partnerships will fail.
- No matter how good your content may be, you still have to earn the right and access to get your content in front of your target audience by building strong relationships.
- Stop looking for copy and paste playbooks to use that are being used by everyone else in the market. If you don’t you’ll just be adding your content and brand to the endless pile of lifeless, gray ooze of things that get ignored. Take a risk and you’ll at least have a chance of sticking out.
- Any partner motion begins with building a relationship with one person. Find the right people to focus on and start one at a time. This is a much quicker way to build real relationships and trust than trying to boil the ocean and make a play for everyone at once.
Sponsored Segment
Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/
Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com
Chapters
00:00 Introducing Justin Gray
00:50 The Origin Story of LeadMD and how they Partnered with Marketo
09:55 The Go-To-Market Cheat Code Book
16:47 Craig makes fun of Justin’s Office
18:12 Lessons on Relationships from The Wild West of the Payment Processing Industry
30:26 The Cycle of Innovation and Imitation
32:09 The Importance of Knowing Your Buyer
40:34 What Venture Capital looks for in Founders
46:50 Building Effective Partnerships
1:05:02 18th Book Plug of the Episode
Sign up for our Newsletter: https://thetransaction.substack.com/
Epic Quotes
- “ What's working is what has always worked which is trusted relationships” - Justin Gray
- “Innovators look for ideas” - Craig Rosenberg
Connect with Justin
- LinkedIn: https://www.linkedin.com/in/inrevenue/
- The Go-to-Market Cheat Code (Book): https://inrevenue.capital/cheat-code/
- Order The Go-to-Market Cheat Code on Amazon: https://amzn.to/4hjtrbA
- In Revenue Capital Website: https://inrevenue.capital/
- The GTM Cheat Code (Podcast): https://inrevenue.capital/insights/?article_category=podcast
Shoutouts
- Essentials/Fear of God Clothing: https://fearofgod.com/
- Focus
- MAAS Impact
- Chris Selland: https://www.linkedin.com/in/cselland/
- LeadMD
- Marketo
- Bill Binch: https://www.linkedin.com/in/bill-binch-302a4a2/
- Margaret Hoogerbeets: https://www.linkedin.com/in/mhoogerbeets/
- Amy Guarino: https://www.linkedin.com/in/amyguarino/
- Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/
- Scottsdale Princess: https://www.scottsdaleprincess.com/
- Josh Wagner: https://www.linkedin.com/in/joshwagneraz/
- Jon Miller: https://www.linkedin.com/in/jonmiller2/
- Jon Miller’s Post about the Tragedy of the Commons in Marketing: https://www.linkedin.com/posts/jonmiller2_mpb2b-b2bmarketing-marketingautomation-activity-7262460572032483328-hs0J?
- Dirty Money, Season 1, Episode 2: https://www.netflix.com/us/title/80118100?s=i&trkid=258593161&vlang=en
- Bessemer: https://www.bvp.com
- Nick Mehta: https://www.linkedin.com/in/nickmehta/
- Marc Beniof: https://www.linkedin.com/in/marcbenioff/
- Founder’s Fund: https://foundersfund.com/
- Asher Mathew: https://www.linkedin.com/in/ashermathew/
- AWS Marketplace: https://aws.amazon.com/marketplace
Love the show? Give us a shoutout on LinkedIn and tell us what you loved!
64 episodes
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1 AI-Powered Cold Calling & SaaS Sales Strategy with Justin Michael & Charles Needham - Ep 60 59:51
59:51 Play Later Play Later Lists Like Liked59:51
Play Later Play Later Lists Like LikedWhat if cold calling isn’t dead—but everything we know about it is? From dissecting permission-based openers to dunking on dated tactics, Justin and Charles make a bold case for why the phone isn’t dead—it’s just misused. Justin Michael, aka the John Wick of executive coaching, is the Founder of the Justin Michael Method and co-author of The Cold Call Algo . Along with being Justin’s Co-Author on Cold Call Algo , Charles Needham is the Founding Account Executive at TitanX and the Founder of Needham Advisory Group. Charles and Justin dig into the unique benefits of cold calling, the evolving role of Sales Development Reps, and where sales orgs should be trying to implement AI sales tools. Critical Takeaways Encouraging SDRs to see cold calling as a means for intelligence gathering rather than merely scheduling meetings can lead to better insights and long-term relationships. The traditional methods of cold calling, like repetitive sales scripts, are losing effectiveness. Incorporate permission-based openers and insightful questions early in the call to create curiosity and engagement. Leveraging AI to clean and target data can dramatically increase the effectiveness of your outreach strategy. By focusing only on prospects who are likely to answer, teams can improve their connect rates and overall outcomes. Train teams to focus on tonality and pacing during calls. Using neutral, calm tones, can help in calming down the prospect's initial resistance and opening up a more natural conversation. Chapters 00:00 Intro 01:09 Introducing Justin Michael and Charles Needham 02:55 Discussing B2B Sales Strategies and Cold Calling 03:37 Justin's Sales Stories and Experiences 08:07 Charles on Modern Sales Challenges 13:22 The Role of AI in Sales 17:10 Cold Calling Techniques and Best Practices 30:29 Debating Cold Call Openers 32:53 Unified Theory of Cold Calling 39:03 Mastering Tonality and Rhythm 56:26 The Future of Cold Calling Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “Cold calling is a mechanism to survey the market and have conversations, rather than going in there like 8 Mile Eminem style—one shot, one opportunity to book a meeting.” - Charles Needham “Problems are isolating by nature. So if you can show someone that it’s common, they’ll open up more.” - Charles Needham “ People buy emotionally, they justify with logic.” - Justin Michael Connect with Justin Michael LinkedIn: https://www.linkedin.com/in/michaeljustin/ Website: https://www.salesborgs.ai/ Get the Book: https://coldcallalgo.com/ Connect with Charles Needham LinkedIn: https://www.linkedin.com/in/charles-needham/ TitanX Website: https://www.titanx.io/ Shoutouts Kai-Fu Lee: https://www.linkedin.com/in/kaifulee/ AI Superpowers: China, Silicon Valley, and the New World Order by Kai-Fu Lee: https://a.co/d/ex6F2Yz David Dulany: https://www.linkedin.com/in/davidkdulany/ Wyzer.ai Mike Bosworth: https://www.linkedin.com/in/mikebosworth/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
1 Explosive Growth of AI Startup Cursor 🔥 - The Direct Deposit - Ep 2 6:15
6:15 Play Later Play Later Lists Like Liked6:15
Play Later Play Later Lists Like LikedIn the second episode of 'The Direct Deposit,' Matt Amundson and Craig Rosenberg dive into the astonishing growth of Cursor, a startup providing an AI code editor for software developers, that has secured three funding rounds and achieved $500 million ARR in less than a year—all without a traditional marketing strategy. Matt & Craig explore how Cursor's product-led growth go-to-market model and simple SaaS pricing tiers contribute to their success in both raising new funding rounds and recurring revenue. Plus, there's a debate over the relevance of a traditional Go-To-Market team for such early-stage startups creating AI products. We also briefly touch upon Matt's favorite movie, John Carpenter's 'Big Trouble in Little China.' Join the newsletter to get new episodes straight to your inbox! Join here: https://thetransaction.substack.com/ Enjoy this episode? Share it with a friend! Believe it or not, even in the tech-fueled world we live in, the number one way podcasts grow is word of mouth . So, if you learned something, lost your cool at something, or laughed at something from the show, give us a hand by sharing this with someone else who will get that same value from the show, regardless if it's education, entertainment, or outrage-inducing.…
1 Actually Actionable Advice For Implementing AI with Jake Dunlap - Ep 59 52:30
52:30 Play Later Play Later Lists Like Liked52:30
Play Later Play Later Lists Like LikedEveryone's talking about how amazing AI can be, but there’s a real dearth of actionable advice on how to actually put generative AI to work for your sales, marketing, customer service, or other go-to-market team. Well, that was until we talked to this week’s incredible guest… Jake Dunlap is truly a thought leader on using AI in B2B go-to-market strategies and is the CEO of Skaled Consulting, a revenue performance agency dedicated to helping B2B companies scale smarter. Jake joins Matt Amundson and Craig Rosenberg to delve into the tactical and practical ways he is implementing AI tools into go-to-market motions and how you can get the benefits of new AI technology. Jake and Matt have both been building some interesting agents and custom GPTs, and they get into how they set them up and how they are using them. Jake discusses why B2B sales leaders need to stop managing by measuring sales rep activity, how to avoid major pitfalls when implementing generative AI tools in your organization, and how to build an efficient and effective outbound strategy today. Also, Craig shares that both of his cars were stolen straight out of his driveway, Matt remembers the name of a consumer product, and Producer Sam interrupts to ask a question about podcasts. Critical Takeaways Train your sellers to think critically. Don't just provide templates. Teach your sales team how to analyze trends, customize outreach, and add value based on their understanding of the buyer's industry and challenges. Encourage creativity and problem-solving skills. Measure outcomes, not just the activities of your sellers. Shift your focus from tracking the sheer volume of sales activities to measuring meaningful conversations and outcomes. The quality of interactions should take precedence over the quantity. Start using AI to improve bottlenecks that you or your team are facing. While there are myriad amazing things you could do with AI, by focusing on the boring, unsexy things that constrain your revenue team, you’ll actually drive greater outcomes for your team. Sellers, try doing the type of outreach that isn’t massively scalable, but that provides immense value and really sticks out. This is likely going to yield better results than hitting ‘send all’ again. For example, you could use new AI tools like Deep Research and NotebookLM to create customized podcasts and white papers tailored to the specific role and industry needs of a contact at a target account. AI is not a go-to-market strategy in and of itself, nor is it something that can be applied in a blanket fashion across every role or function. Let sellers play to their strengths. For example, some reps are great on video, while others excel on the phone. Don’t force every sales rep into the same volume-driven mold. Focus on outcomes, not activities. Don’t wait for Enablement to hold your hand and train you on using AI. As Jake said, “ sales leaders, executives, listen to me. You have to learn this yourself. You cannot outsource this through rev ops.” Why is that? Because AI is more than just another tech tool, it’s a fundamental shift in problem-solving. Don’t sit around waiting for a playbook—experiment, build, and iterate. Training wheels are for losers… and small children. Chapters 00:00 - Episode Preview 00:36 - The Fast & The Furious: Silicon Valley Drift 07:39 - Two Insightful Examples of How B2B Companies are Using & Operationalizing Gen AI 11:41 - Why B2B Sales Reps Need to Start Using AI for Account Research & How to Get Started with New AI Tools 13:36 - How to Build AI Agents for Each Buyer Persona & How Matt is Using AI as a Chief Marketing Officer 16:08 - The Power of Building Custom AI Agents for Revenue Growth 22:22 - B2B Sales Leaders are Still Getting Stuck on Activity Metrics, When They Should Measure Impact 30:04 - How to Construct a Successful B2B Outbound Strategy in the Current Market 37:01 - How Will Anthropic and OpenAI’s Custom GPTs Integrate with Existing SaaS Tools & Will Gen AI Tools Replace the Go-To-Market Function as We Know It? 42:01 - What Hurdles to Avoid When Implementing AI Tools in Your Company & Why Leaders Need to Stay on Top of AI Advancements Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “Stop asking the question, ‘What’s our AI go-to-market strategy?’ It’s not the right question.” - Jake Dunlap “The goal are the outcomes, not the activities.” - Jake Dunlap “Outbound never ends. You cannot take a project-based mindset to outbound.” - Jake Dunlap Connect with Jake Dunlap LinkedIn: https://www.linkedin.com/in/jakedunlap/ Website: https://skaled.com/ The Innovative Seller (Jake’s Book): https://www.jakedunlap.com/the-innovative-seller Shoutouts Dirty Mike and The Boys: https://youtu.be/1FkK8ZFE7Y0?si=WpJ9miacA2CdLq0u NotebookLM: https://notebooklm.google/ The Goal: A Process of Ongoing Improvement by Eliyahu M. Goldratt & Jeff Cox: https://a.co/d/03F3RE2 Matt Heinz: https://www.linkedin.com/in/mattheinz/ Matt’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/how-to-implement-ai-in-your-go-to?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Sydney Sloan: https://www.linkedin.com/in/sydsloan/ Sydney’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false The Club: https://store.winner-intl.com/the-original-club-p2.aspx Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
1 What Made RevFest 2025 Such a Great B2B Event? - The Direct Deposit by The Transaction - Ep 1 5:31
5:31 Play Later Play Later Lists Like Liked5:31
Play Later Play Later Lists Like Liked1. We are testing a new The Transaction product - The Direct Deposit. The idea is to take something that happened that week and one host asks the other host 5 questions. The result is a 5 minute quick hit. 2. For this week's Direct Deposit, we cover RevFest. I'll give you the high level: 🐰 Jen Igartua and the Go Nimbly team killed it. Also, I am leading an unauthorized effort to rename it LoveFest 2026 but Matt Amundson keeps killing it. Lesss go! This is the first edition of The Direct Deposit presented by The Transaction. ======================================== Subscribe to the Newsletter: https://thetransaction.substack.com/ Follow the Show: - Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ - Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ - Sam's LinkedIn: https://www.linkedin.com/in/sam-guertin/ - The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ - The Transaction Website: https://thetransactionpod.com/ Ways to Tune In: - Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz - Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 - YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1 - More Options: https://thetransactionpod.com/subscribe…
1 Founder-Led GTM, Growth Bets, & Why Stories Win With Scott Albro - Ep 058 47:02
47:02 Play Later Play Later Lists Like Liked47:02
Play Later Play Later Lists Like LikedScott Albro is back in The Transaction hot seat—and he’s not here to play nice. Scott brings a flame-thrower to traditional playbooks, urging GTM leaders to experiment wildly, think like founders, and stop chasing MQLs like it’s still 2014. Craig and Matt get Scott talking about everything from AI-driven storytelling to "vibe marketing," with detours through SDR history lessons, Red Bull stunts, and the existential crisis of printer ownership. If your go-to-market motion still depends on intent data and white papers… this episode might hurt (in a good way). Also, Craig breaks his keyboard, Matt mentions a little company he likes to call Red Bull, and Producer Sam desperately attempts to curry favor with Scott. Critical Takeaways The next wave of breakout companies will be driven by founders who embed themselves deeply into the Go-To-Market engine, not just product. Founder-led GTM creates authenticity, speed, and unmatched customer resonance. High-performing Go-To-Market teams in SaaS-land are shifting from one-size-fits-all playbooks to an experimentation mindset. It’s about making bold bets, measuring ruthlessly, and scaling what works, not chasing the hack of the week. Most so-called intent data is internet exhaust, not evidence of real purchase behavior. The best GTM orgs lead with narrative clarity, tying their solution to a broader shift in the world, anchoring it in customer pain, and delivering it with conviction. Skip this, and no one remembers you. Stunt marketing has a place in B2B SaaS. Think viral launches, bold storytelling, and emotional engagement. It’s not about gimmicks, it’s about being memorable in a world flooded with sameness. Chapters 00:00 Episode Preview 03:30 – The Go-To-Market Founder Concept 07:00 – How Modern Go-To-Market Orgs Win 13:00 – Growth Bets: What They Are and Why They Matter for B2B Marketers 17:00 – Crafting a Resonant Story for your B2B brand 21:00 – Aligning Product and Go-To-Market Motions (Finally) 25:00 – Convincing B2B Startup CEOs to Experiment 30:00 – Bland’s Viral Growth and the “Stunt Marketing” Debate 36:00 – Storytelling Frameworks That Actually Work for Startups 42:00 – Lethal Weapon Posters and Swarms of Bees Epic Quotes Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “If you're not reinventing your Go-To-Market org, you need to have a look in the mirror.” - Scott Albro “ Founders can just do things that other people can't. ” - Scott Albro Connect with Scott LinkedIn: https://www.linkedin.com/in/scottalbro/ Shoutouts & Resources Mentioned Skosh: https://www.merriam-webster.com/dictionary/skosh Skosh Usage over time: https://books.google.com/ngrams/graph?content=skosh%2Csmidge%2Ctad%2Ciota%2Cmodicum%2Cwhit%2Cscruple%2Csmidgeon%2Cwee%2Cfathom&year_start=1800&year_end=2022&corpus=en&smoothing=3 Bland Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ Tricia Gellman: https://www.linkedin.com/in/gellmansfmarketing/ Lena Waters: https://www.linkedin.com/in/lenawaters/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
1 Overcoming Your 'Go-To-Market Midlife Crisis' with Craig & Matt - Ep 57 55:11
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Play Later Play Later Lists Like LikedThat’s right, no guest on this one, but not to worry, it’s just as insight-filled, yet off the rails, as all of our other episodes that you’ve come to know and love. Co-Hosts Matt Amundson and Craig Rosenberg discuss coming to terms with their go-to-market mid-life crises and how they have gotten up to speed on the latest AI advancements to help them get back in the game. Craig and Matt dig into how they’re using AI tools to create things like AI buyer personas, the impact B2B events are having, and what the new go to market playbook is beginning to look like. Also, Matt reveals his devious guilty pleasure and Craig shares how he lost his children in the desert. Critical Takeaways Instead of prompting AI like a search engine, leaders should teach their teams to treat it like a colleague. Matt’s breakthrough came when he asked ChatGPT how to build personas and what information it needed to do so. By asking “how do I build X?” instead of “give me X,” teams unlock faster, higher-quality outcomes. Adopt a “Shock & Awe” mindset to break through. The market is saturated and fatigued—practical content alone isn’t enough. As Craig put it, GTM teams need to pair insight with surprise to break buyers’ patterns. Leaders should push teams to experiment with bolder formats, storytelling, or AI-powered personalization that “breaks the frame.” Account Research with AI is now table stakes for sales and marketing teams. Using AI for account research (before, during, and after sales calls) is no longer optional. Craig emphasized this is the new baseline expectation. If your team isn’t using tools like ChatGPT or Perplexity to prep on accounts and individuals before outreach, you’re behind. Before adopting any AI vendor solution, ask: “Can my team do this directly in ChatGPT or another general model?” As Craig noted, many startups at SaaStr were pitching account prep workflows that anyone can already do with a simple prompt. Chapters 00:00 Episode Preview 03:30 The GTM Midlife Crisis Hits – Why the old playbooks stopped working 06:15 Building a New Playbook with AI in the Go-To-Market Hacker era 08:45 Matt’s AI Buyer Persona Workflow – How to build and deploy AI agents for feedback 13:15 Talk to Your AI Tools Like People 17:00 999/1000 Accuracy Rate – Why AI is now a mission-critical content editor 25:30 Account Research is the New Minimum – How GTM teams are winning with better prep 30:00 Matt & Craig just Want to Watch the World Burn 37:00 Events Are Back, Baby – People crave new insights and in-person energy 40:00 LinkedIn has changed, but it is still the social platform of choice for B2B brands 45:00 Video Content: Raw vs. Polished – When it’s time to scale production (and when DIY still wins) 50:00 Lost in the Desert: A GTM Parable – Craig’s real-life ATV crisis ends with a 10-year-old roasting him Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ It's the age of the Go-To-Market hacker.” - Craig Rosenberg “ Everybody needs to create a custom GPT. And if you want to know how to do it, just ask it. How do I create a custom GPT here?” - Matt Amundson Shoutouts Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ Kristina McMillan: https://www.linkedin.com/in/kristinamcmillan/ David Boskovic: https://www.linkedin.com/in/dboskovic/ Jill Rowley: https://www.linkedin.com/in/jillrowley/ Jill Rowley’s tweet calling Craig’s Blackberry in 2012: https://x.com/jill_rowley/status/187231284970536960 SaaStr Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ Antonio Garcia: https://www.linkedin.com/in/antonio-garcia-18b912220/ Copy.ai Klarity: https://www.klarity.ai/ Sydney Sloan: https://www.linkedin.com/in/sydsloan/ Mandy Dhaliwal: https://www.linkedin.com/in/1mandydhaliwal/ Jake Dunlap: https://www.linkedin.com/in/jakedunlap/ James Kaikis: https://www.linkedin.com/in/jameskaikis/ Jordan Crawford: https://www.linkedin.com/in/jordancrawford/ Jordan’s Episode: https://open.substack.com/pub/thetransaction/p/inverting-your-go-to-market-strategy?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
1 Crafting an Exceptional Event Marketing Strategy with Amy Holtzman - Ep 56 52:49
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Play Later Play Later Lists Like LikedB2B marketers keep making the same mistakes when it comes to events, only to end up asking why they didn’t see any ROI. Thankfully, we knew just the right person to help you improve your field marketing game… Amy Holtzman is the Chief Marketing Officer of CHEQ, the leader in go-to-market security, and one of the best B2B marketing leaders in SaaS, especially when it comes to creating unforgettable experiences. Amy joins co-hosts Craig Rosenberg and Matt Amundson to explore how to plan an event marketing strategy that doesn’t suck, why you need to think beyond the vendor booth at a conference to see real ROI, and even how traditional paid search is holding up amidst the onslaught of AI advancements. Also, Craig says something he immediately regrets, Matt makes an unsettling insinuation, and Producer Sam calls someone a naughty word. Critical Takeaways Events are still alive, if you are willing to put in the work to make them stand out. You can’t just “show up and hope.” Great booths need real strategy, creative hooks, and a human-first approach that makes people actually want to engage. Whether selling B2B or B2C, even strong demand dies in broken systems. Want revenue? Get your backend in order first so you can deliver remarkably good customer experiences Prospects are already using ChatGPT to build vendor shortlists. If your GTM doesn’t account for AI-powered discovery, you’re already behind. Despite the hype around AI, traditional paid search drove record enterprise deals for CHEQ in Q1 of this year, especially long-tail keywords. Don’t ditch the old toolbox just yet. Chapters 00:00 - Episode Teaser 00:34 - Amy’s Amazing Hat, Chain Restaurant Pub Crawls, & the Apollo Theater 10:36 - Introducing Amy Holtzman, Chief Marketing Officer at CHEQ 13:46 - Lessons to Learn from the Worst Sales Experience Ever 25:53 - Search is Still Driving A Surprising Amount of Enterprise Deals 30:50 - Breaking Down the New G2 Research on B2B Buying Behavior & How AI is Impacting Vendor Shortlists 35:08 - How to Get More ROI from your Event Strategy & Field Marketing Mistakes to Avoid 39:46 - Sponsoring Niche Events can Pack a Massive Punch for Smaller B2B Brands 44:44 - Thinking Beyond the Booth When Planning out Your Event Strategy Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ Really strong quality work and great execution never goes out of style, no matter what the trend is and what's working.” - Amy Holtzman “If you want to sell things, make sure you have enough salespeople.” - Amy Holtzman “I rub the thing” - Craig Rosenberg Connect with Amy LinkedIn: https://www.linkedin.com/in/aholtzman/ Website: https://cheq.ai/ Shoutouts Every Little Step I Take by Bobby Brown: https://youtu.be/P0FKzPfsxA4?si=o3k9Iepu3KwnP1Aa Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/ Jessica Lin: https://www.linkedin.com/in/jessicalin8/ Amy’s Episode on The Drafting Table: https://www.thedraftingtablepodcast.com/content/conferences-arent-a-vibe-theyre-a-sales-channel-how-to-actually-make-them-worth-it-with-amy-holtzman-cmo-at-cheq Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ G2 Buying Behavior Report: https://learn.g2.com/2025-g2-buyer-behavior-report Sydney Sloan: https://www.linkedin.com/in/sydsloan/ Scott Albro: https://www.linkedin.com/in/scottalbro/ The Tonga Room: https://www.fairmont-san-francisco.com/dine/tonga-room-hurricane-bar/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
1 Inverting your Go-To-Market Strategy Thinking with Jordan Crawford - Ep 55 51:46
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Play Later Play Later Lists Like LikedAI use cases & tactics are moving at a million miles per hour which can make it hard to adopt some of these amazing innovations into your go-to-market strategy. Thankfully, we knew just the guy to have on the show to help us put into practice what otherwise could seem like technological mumbo, and or jumbo. That man’s name is Jordan Crawford, the Founder of Blueprint GTM and one of the foremost go-to-market engineers innovating B2B sales and marketing on the cutting edge of AI advancements. Jordan joins co-hosts Craig Rosenberg and Matt Amundson to dive into where we’re thinking about our go-to-market strategy and tech stack in the wrong way, how to segment cold outbound leads in an effective, yet scalable way based on pain, and how to evolve your revenue organization to excel in the new, ai-powered world. Also, Craig shows off his sandwich shop shirt, Matt gets on yet another soapbox, and Producer Sam is asked for his opinion. Critical Takeaways Identify specific, narrow segments by understanding unique heuristics that indicate a need for your product. For instance, identifying complex sales teams with high traffic who would benefit from LeanData's routing solutions is more effective than broad targeting. You need to understand your customers and their pain before bringing in tools like Clay or ZoomInfo. Sales leaders should spend time with SDRs to gain insights on what truly resonates with prospects, ensuring that any data or tools used are enhancing proven strategies rather than replacing deep understanding. The burden placed on SDRs to make sense of complex data without adequate support is a recurring issue. Leaders should simplify data insights and ensure SDRs are equipped with actionable, digestible information, alleviating stress and improving effectiveness. Adopt a 'pain-qualified' segmentation approach. Identify segments that not only fit demographic profiles but also exhibit specific pain points that your product can address, such as complex routing needs in high-traffic sales teams for LeanData. This ensures messages are highly relevant and more likely to result in conversions. Sponsored Segment Lorem ipsum Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Introduction: The Intimidating Box 01:07 Mr. Pickles and Misadventures in Pocket Dialing 04:42 Craig’s Midlife Go-To-Market Crisis 05:31 What’s broken with the Old Go-To-Market Playbooks 07:30 What is The New World of Sales and AI 13:04 Segmenting and Targeting with Data 16:43 Permissionless Value Prop in Action 23:25 The List is the Message 25:47 Methodology and AI Integration 26:55 Understanding Customer Segments 29:56 Challenges in Sales and Marketing 33:18 Effective Campaign Strategies 35:16 Adapting to AI and Market Changes 38:37 Purpose of Niche Targeting and Success Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “The list is the message.” - Jordan Crawford “Never in my life has there been a more intimidating box than the ChatGPT, Claude, Gemini entry box because for the first time in our lifetimes, and maybe human history, we are the limiters.” - Jordan Crawford New Terms Pain Qualified Segment: Two to five unique heuristics, often that imply tension. Connect with Jordan LinkedIn: https://www.linkedin.com/in/jordancrawford/ Website: https://blueprintgtm.com/ YouTube: https://www.youtube.com/@BlueprintGTM Jordan’s Latest Course: https://pvp.blueprintgtm.com/subscribe Shoutouts Scott Albro: https://www.linkedin.com/in/scottalbro/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
1 How to Implement AI in Your Go-To-Market with Matt Heinz - Ep 54 57:37
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Play Later Play Later Lists Like LikedMatt Heinz, the President of Heinz Marketing, is a top 50 Sales & Marketing Influencer and a prolific thought leader in the B2B marketing space. Matt digs into why B2B marketers should invest more in brand as the AI Age progresses, whether the Chief Marketing Officer should report to the Chief Revenue Officer, and why B2B marketers are so terrible at naming products and concepts. Also, Craig ponders the meaning of parabolas, Matt ranks the best men’s hair in B2B Marketing, and Producer Sam gets confused by Craig talking about bats. Critical Takeaways Develop a structured approach to AI adoption in Go-To-Market strategies. Instead of engaging in 'random acts of AI,' organizations should create an accountability chart detailing which jobs are better suited for machines and which require human intervention. Personal connections and credibility can differentiate a brand in a noisy market. Efforts should be made to maintain and build these relationships alongside leveraging scalable technology. While marketing attribution is important, it should not solely focus on credit for past actions. It should be used to create a more predictable and reliable path towards future outcomes. Go to market teams need to look at attribution as a tool for driving the right behaviors and actions, rather than merely analyzing past performance. Signals, including “intent signals”, need to be understood in context and not treated as immediate leads. Revenue teams should use signals to inform their understanding of where a prospect is in the buying journey, rather than assuming all signals indicate readiness to buy. This nuanced understanding can improve targeting and engagement efforts. Even as AI and automation take on more tasks, creativity and strategic thinking remain irreplaceable. Teams should focus on leveraging AI for efficiency while reserving creative and complex problem-solving tasks for human talent. This balance can drive innovation and maintain a competitive edge. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Episode preview 00:30 Craig Goes Batty and Some Auction Antics 04:13 Introducing Matt Heinz, President of Heinz Marketing 08:07 B2B Marketers are Terrible at Naming Concepts, Products, and Strategies 19:16 Should CMOs Report Up to CROs in B2B SaaS? 22:03 Ranking the Best Hair Amongst Men in B2B & Matt Confesses to Rocking a Mullet 27:27 How Go-To-Market Teams are Using AI & Evolving Their GTM Strategy with AI 37:13 Trust & Personal Relationships are Differentiators in the Age of AI Marketing Tools 42:11 The Role of Data & The Cloud Data Warehouse in B2B Marketing Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ We shouldn't be guessing anymore, we should be using the agents to tell us how to improve right away” - Matt Heinz “ If I have more noise and less time, who am I going to prioritize? It's the people I enjoy. It's the people I trust. It's the people I like. That's going to be a huge differentiator moving forward.” - Matt Heinz “ I don't want anybody to think that I'm not down with intent signals. I'm down with signals because right now the hardest thing in the world to do is engage.” - Craig Rosenberg “If you are looking for the solution in the tool, you're bound to fail.” - Matt Amundson Connect with Matt Heinz LinkedIn: https://www.linkedin.com/in/mattheinz/ Website: https://www.heinzmarketing.com/ Shoutouts Bat Tours in Austin: https://www.austintexas.org/things-to-do/outdoors/bat-watching/ Bert Kreischer’s Raffle Story: https://youtu.be/EsCadHpBdkY?si=GDRoQpWQ9B1Z_55l Coffee with Brent & Matt: https://www.heinzmarketing.com/events/podcast-coffee-with-brent-adamson-matt-heinz/ Joe Chernov: https://www.linkedin.com/in/jchernov/ Steve Woods: Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon’s Episode: https://open.substack.com/pub/thetransaction/p/building-trust-and-reputation-in Lars Nilsson: https://www.linkedin.com/in/lanilsson/ Lars’ Episode: https://open.substack.com/pub/thetransaction/p/setting-up-successful-b2b-saas-sales Ted Purcell: https://www.linkedin.com/in/tedpurcell/ Adam Robinson: https://www.linkedin.com/in/adam-robinson-4b156810/ Adam’s Episode: https://open.substack.com/pub/thetransaction/p/asymmetrical-marketing-and-personal Anthony Kennada: https://www.linkedin.com/in/akennada/ Chris Walker: https://www.linkedin.com/in/chriswalker171/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Mary Meeker: https://www.linkedin.com/in/mary-meeker-5823ba48/ Simbe Robotics Mperativ Brent Adamson: https://www.linkedin.com/in/brentadamson/ Brent’s Episode: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
1 Setting up Successful B2B SaaS Sales Development Orgs with Lars Nilsson - Ep 53 1:00:11
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Play Later Play Later Lists Like LikedNot a long time ago in a Silicon Valley not too far away, the sales infrastructure of almost every startup was an immature, undisciplined mess… Until a certain former printer salesman turned up in town… Lars Nilsson is the Founder and CEO of SalesSource, but you probably know him from his legendary run as the VP of Global Sales Development at Snowflake. To Craig, Lars is, “one of the masters of the universe in sales development and inside sales and business, and clearly very fit.” Lars joins co-hosts Craig Rosenberg and Matt Amundson to discuss how we got to the current state of sales training and enablement in B2B SaaS, why the GTM Engineer role is the next hire you need to make to improve your revenue team, and whether having B2B sales reps roleplay with AI avatars is the way forward or just a waste of time. Also, Craig relives stories of his past mastication, Producer Sam fights yet another losing battle, and Matt warns everyone that, “ we're going to go deep. We're going deep.” Critical Takeaways Recognize and elevate the Sales Development Representative (SDR) function within the organization. CEOs and senior leaders should regularly acknowledge the impact SDRs have on pipeline generation. Simple acts of recognition can significantly boost team morale and performance. Create a systematic process to gather and disseminate insights and customer feedback from the front lines of sales. SDRs interact with numerous prospects daily, and their feedback can inform product development, marketing strategies, and sales tactics. Ensuring this information reaches executive levels can align the organization’s initiatives more closely with market needs. Giving your sales team more ‘at-bats’ to practice and hone their craft results in better sellers. Leverage AI-based tools like role-playing bots to enhance SDR training. These tools can provide a scalable, less intimidating way for SDRs to practice their pitches and objection handling. Encourage cross-departmental learning within your org. Facilitate opportunities for SDRs to learn from other teams, such as marketing, operations, and customer success. This cross-training can develop well-rounded employees and ensure smoother transitions when SDRs move into new roles within the company. Consistently produce and share content that showcases successful customer stories and product use cases. Having a dedicated resource person, like the retired beat reporter who worked with Lean Data, can ensure continuous content production that drives engagement and educates prospects. Encourage a culture where continuous learning and improvement are part of daily operations. Regularly update training programs and technology stacks, and stay abreast of the latest trends and tools in sales and marketing to maintain competitiveness. Sponsored Segment ~Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 - Episode Preview 00:35 - Craig Eats like Cookie Monster 03:13 - Introducing Lars Nilsson, the Founder & CEO of SalesSource and Former VP of Global Sales Development at Snowflake 07:46 - The Genesis of Sales Development in SaaS & How it Expanded on Account-Based Marketing Concepts 13:23 - How Xerox Trained Their B2B Sales Team and What Startups Should Learn from Their Success 21:34 - The Emerging GTM Engineer Role & The Impact Its Having on B2B Sales Teams Using AI Tools 34:59 - Should B2B Startups Try to Replicate the SDR Academy from Snowflake 38:17 - How Startup Leaders Can Elevate the SDR Role & Why They Must Show Their Appreciation for this Critical Function 45:42 - The Importance of AI Roleplaying Tools for Training B2B Salespeople 54:11 - Startups Founders Should Play a More Active Role in Developing Their Go To Market Strategy Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ I just think that Snowflake with 300 SDRs today, maybe in two years, they'll have 50. But each one will be able to punch above, like they are five individuals because of all the automation.” - Lars Nilsson “ One Go-To-Market engineer today is going to make five SDRs punch like they're 25.” - Lars Nilsson Connect with Lars LinkedIn: https://www.linkedin.com/in/lanilsson/ SalesSource Website: https://salessource.com/ Shoutouts Stuart Silverman: https://www.linkedin.com/in/stuart-silverman-32132/ Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Karan Singh: https://www.linkedin.com/in/karan-singh-29269015/ Travis Henry: https://www.linkedin.com/in/travisjhenry/ Brendan Short: https://www.linkedin.com/in/brendan-short/ Pete Kazanjy: https://www.linkedin.com/in/kazanjy/ Jason Vargas: https://www.linkedin.com/in/jasonvargas/ John Barrows: https://www.linkedin.com/in/johnbarrows/ Becc Holland: https://www.linkedin.com/in/beccholland-flipthescript/ Hyperbound: https://www.hyperbound.ai/ Ralph Barsi: https://www.linkedin.com/in/ralphbarsi/ Morgan Ingram: https://www.linkedin.com/in/morganjingramamp/ Kevin Dorsey: https://www.linkedin.com/in/kddorsey3/ Trish Bertuzzi: https://www.linkedin.com/in/trishbertuzzi/ Scott Barker trying to book a meeting with Avarra’s AI Avatar Role Play: https://youtu.be/90EQSxcIhqc?si=gKDiVmsnadrsk_IY Tavus: https://www.tavus.io/…
1 Building a Customer-Centric Go-To-Market Strategy with Lauren Goldstein - Ep 52 52:32
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Play Later Play Later Lists Like LikedMost B2B brands (yes, probably yours) think that they’re ‘customer-centric’, and yet none of them ever stop droning on and on about their product and its ‘revolutionary’ features. Lauren Goldstein is the Chief Growth Officer of Winning by Design and Co-Founder, Board Member, Chair of the Board of Directors for Women in Revenue. Lauren joins co-hosts Craig Rosenberg and Matt Amundson to chat how B2B sellers and marketers can connect with buyers in the way buyers want them to, why having a diverse leadership team is an invaluable asset for any startup, and why “Strategic RevOps” is enabling breakthrough growth for SaaS startups. Also, Craig shocks the world by caping for his portfolio companies’ sales pitches, and Matt mentions the production design aesthetic of a niche director. Critical Takeaways Implement structured mentorship programs in your org where experienced team members can guide less experienced colleagues, as this can lead to increased job satisfaction and retention, on top of the personal and professional development of your whole team. Instead of spending time on a sales call waxing poetic about the ‘revolutionary’ features of your product, use that time to ask your prospect what success looks like for them. How are they measured as a success or failure? Uncover that ideal state and help them understand how your product can get them there, provided it actually can; otherwise, don’t waste their time and yours. Consider using ‘Reverse Demos’, where instead of showing off your product right away, you have the customer outline their current processes and challenges. While this approach might not work with all types of buyers, it could be effective in understanding complex systems and better tailoring your pitch to the customer's actual needs. Cross-functional alignment across your go-to-market team is crucial. Sales, marketing, product, and finance teams need to work collaboratively, understanding each other’s objectives and challenges. Regular inter-department meetings to align goals and strategies help everyone move in the same direction towards shared business goals. Companies that have strategic RevOps roles are better at aligning their sales and marketing efforts with financial and operational goals, ultimately driving growth and operational efficiency. Sponsored Segment Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 - Episode Preview 00:30 - Are the Angels a Real Team & Breaking Down the Backgrounds 03:24 - Introducing Lauren Goldstein, Chief Growth Officer of Winning By Design & Co-Founder of Women in Revenue 06:36 - The Origin Story of Women in Revenue (The group, not the concept) 18:17 - The Immutable Impact Diverse Teams in Business 23:43 - B2B Tech Brands Are NOT Connecting Buyers in the Ways That SaaS Buyers Want 31:39 - What is a ‘Reverse Demo’ & Why is Gartner Analyst Dan Gottlieb Recommending it 36:00 - Revenue Growth in SaaS Comes Back to Identifying the Right Buyers 40:43 - The Critical Role of Rev Ops in B2B Go-to-Market Strategy for SaaS 44:00 - Strategic Rev Ops: The Key to Integration & Go-To-Market Alignment Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ Managing multiple stakeholders in an enterprise sale is not a new thing. But it's more than managing multiple stakeholders, it's really about helping to facilitate a conversation where they're all understanding the problem in the same way and can connect back to a common denominator.” - Lauren Goldstein “ There is no greater liar as a buyer, than a marketer.” - Matt Amundson (A Marketer) Connect with Lauren LinkedIn: https://www.linkedin.com/in/laurengoldstein/ Winning by Design Website: https://winningbydesign.com/ Women in Revenue Website: https://womeninrevenue.org/ Shoutouts Sydney Sloan: https://www.linkedin.com/in/sydsloan/ Sydney’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-strategic-marketing-with Katharine Reagan: https://www.linkedin.com/in/katharine-reagan/ Shari Johnston: https://www.linkedin.com/in/sharijohnston/ Jen Dimas: https://www.linkedin.com/in/jenpd/ Tracy Eiler: https://www.linkedin.com/in/tracyeiler/ Jim Walker: https://www.linkedin.com/in/jwwalker/ Robert Koehler: https://www.linkedin.com/in/rkoehler/ Radius Marketo Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ InsideView Babcock Jenkins Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan’s Episode: https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb Miro Mark Kosoglow: https://www.linkedin.com/in/mkosoglow/ Mark’s Episode: https://open.substack.com/pub/thetransaction/p/unlocking-sales-success-creativity Kelly DeHart: https://www.linkedin.com/in/kelly-dehart-18b63315/ Tom Murtaugh: https://www.linkedin.com/in/tom-murtaugh-1729b09/ Colin Gerber: https://www.linkedin.com/in/colinsgerber/ Socure Adam B. Needles: https://www.linkedin.com/in/abneedles/ Adam’s Episode: https://open.substack.com/pub/thetransaction/p/the-new-go-to-market-blueprint-with Annuitas Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
1 Insight-Driven Outreach Beats Personalization with Ana Leyva - Ep 51 52:18
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Play Later Play Later Lists Like LikedAna Leyva advises early-stage startups at Pear VC on their go-to-market strategy to help them build stunning sales motions that set them up to scale. Ana provides pre-seed and seed startups with her first-hand experience as a seasoned operator with past roles at tech unicorns Box, ServiceTitan, and Vanta. Ana joins Co-Hosts Craig Rosenberg and Matt Amundson to delve into how to transition beyond a founder-led sales motion without losing their special perspective, why insight-driven outreach beats crappy sales personalization in B2B, and the two foundational pillars that you need to have in place to build a strong go-to-market strategy. Additionally, Ana details the importance for founders to be extremely disciplined with their Ideal Customer Profile and who they allow to steer the course of the future of their company. Also, Craig gets a ton of text notifications, and Matt muses about buying Craig a present for Easter. Critical Takeaways The crappy bit of personalization you grabbed from LinkedIn and added to your stale cold outbound email is not going to set you apart. ‘We went to the same school’ doesn’t help that decision maker develop a solution to the problems they’re facing. Rather than relying on bare-minimum ‘personalization’, put your thinking cap on and reach out with a business insight that can actually help your prospect learn more about their business, understand their problem better, or make a more informed decision. As hard as it can seem to turn down customers early on, founders need the discipline to focus on prospects who will truly benefit from their product, and saying no to the wrong fit is crucial for building long-term customer relationships. The bedrock of your go to market strategy should be built upon endless customer obsession and very strict ICP (Ideal Customer Profile) parameters. That ensures you deeply understand the pain your customer solves and can build a product to solve that pain effectively. Don’t just let your customers come to you, you need to pick the right protagonists for the epic narrative that you are creating for yourself and your customers. Be picky about who you allow to join and steer the arc of this grand story you are embarking on. Sponsored Segment Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 - Episode Preview 00:20 - Squishy Pineapples & The 1995 UCLA Bruins 04:01 - Introducing Ana Leyva, GTM Leader at Pear VC 08:29 Selling at B2B Conferences on the Road as a New Mom 11:32 - Focus on Providing Value, not on Bland “Personalization” 21:33 - B2B SaaS Founders Need to Rewrite New Go To Market Playbooks 27:24 - Scaling Your Sales Team & Shifting from Founder-led Sales 34:53 - Discipline is a Founder’s Best Friend & Going Narrow is the Way to Win as a Startup 45:06 - Is Cold-Calling Coming back in Style for SaaS Sales Teams? Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “I am sick of personalized emails.” - Ana Leyva “I always tell our founders, you’re not selling for the initial close; you’re selling for the renewal.” - Ana Leyva Connect with Ana LinkedIn: https://www.linkedin.com/in/analeyva/ Pear VC Website: https://pear.vc/ Shoutouts AJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ Brandon Redlinger: https://www.linkedin.com/in/brandonredlinger/ Brent Adamson: https://www.linkedin.com/in/brentadamson/ Brent’s Episode: Chris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris’s Episode: Jen Allen-Knuth: https://www.linkedin.com/in/demandjen1/ Jason Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Jason’s Post on LinkedIn: https://www.linkedin.com/posts/jasonmlemkin_so-theres-a-lot-of-angst-on-linkedin-about-activity-7308223252420509697-EJCS Stevie Case: https://www.linkedin.com/in/steviecase/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Gong Scott Barker: https://www.linkedin.com/in/ssbarker/ Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
1 Selling to the Enterprise From the Start with Sheila Stafford - Ep 50 53:17
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Play Later Play Later Lists Like LikedSheila Stafford is the Founder and CEO of TeamSense and joins Co-Hosts Matt Amundson and Craig Rosenberg to dig into how to land enterprise clients as a startup, how to build out a B2B sales team from scratch, and why NRR (Net Revenue Retention) is the most important metric for founders to focus on. Shelia also shares why she thinks email is a dead sales channel and why she is betting on modern PR tactics for growing TeamSense. Also, Craig shares his Instagram Shopping habits, Matt shows off his support for the Dodgers, and Sam the Producer tells a story about a field trip he went on. Critical Takeaways NRR (Net Revenue Retention) is the most important metric for startup founders because it is a direct reflection of customer love, which is the only real moat in software. When it comes to assessing new opportunities and verticals, founders need to ask themselves if it’s worth taking on a crappy client to get a short-term revenue bump, but a longer-term decrease in NRR. For Sheila and TeamSense, the answer has been a resounding, “No.” Discipline is such an important factor for founders in a number of ways, including niching down on a single vertical. This can ensure that your resources are optimally utilized, maintain a strong product-market fit, and ensure long-term sustainability and scalability of your offerings. Deep subject matter expertise in the industry you are trying to serve is invaluable. For example, Sheila's extensive experience in manufacturing allowed her to understand and address the unique challenges faced by her customers. This level of insight informed the development and marketing of TeamSense, ensuring the product met real, pressing needs. Concentrate all resources on one primary vertical before expanding to adjacent markets. TeamSense initially focused solely on manufacturing and logistics, applying all their efforts there until other verticals started showing interest naturally. This approach ensures a strong foundation before diversification. Implement a culture of continuous improvement and maintain active feedback loops. Sheila listens to her team’s Gong calls to ensure messaging remains effective and aligned with customer needs, and she provides direct feedback to her team. This practice ensures that the team continuously refines their approach based on real-time data and feedback. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 - Preview & Craig’s Christmas related-shirt 04:21 - The Sometimes Life-saving Impact Founding a Company Can Have 10:03 - Email is a Mostly Dead Channel 14:17 - How to Get Your First Enterprise SaaS Deal & TeamSense’s Founding Story 20:38 - Learn Your Customers' Native Language & Use It When Communicating Impact 27:24 - Why Building Deep Expertise & Building Something For Someone is Critical for Startups 33:11 - How Do You Measure the Value Your Product Delivers to Customers & Why Founders Need to Focus on NRR 35:45 - How to Drive Alignment Between Founders and Their Boards 38:53 - How to Build out a Sales Team from Scratch & Growing Beyond Founder-Led Sales 45:16 - Modern Marketing Experiments & Can PR Still Pack A Punch? Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ Net revenue retention KPIs are probably one of the most important things that you should pay attention to as a founder.” - Sheila Stafford Connect with Sheila LinkedIn: https://www.linkedin.com/in/sheila-stafford-451976b/ Website: https://www.teamsense.com/ Shoutouts Fortive Vanta Christina Cacioppo: https://www.linkedin.com/in/ccacioppo/ Brett Queener: https://www.linkedin.com/in/brettqueener/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
1 Double Down on What’s Working & Stay Focused with Eric Spett - Ep 49 49:08
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Play Later Play Later Lists Like LikedIs your main go-to-market channel driving sustainable growth? Good, double down on it, don’t start splitting up your resources into a bunch of other directions. Eric Spett is the Founder and CEO of Scalebound, providing operator-led coaching that helps CEOs scale with clarity and lead with confidence. Many in the audience may know Eric better as the Co-Founder of Terminus and his work evangelizing Account-Based Marketing. Eric joins co-hosts Craig Rosenberg and Matt Amundson to discuss the importance of focus for founders, why you shouldn’t wait to start selling until you find the perfect pricing model, and the power of in-person events and communities. Also, Craig starts hearing voices and Matt shares his encounter with Andre 3000 in an Atlanta Shake Shack. Critical Takeaways Stay focused on your primary demand channel. So many companies shift focus to secondary channels prematurely. If a primary channel like organic social selling on LinkedIn or cold calling is working well, it’s crucial to thoroughly exploit this channel before diverting resources to a new one. Avoiding "shiny object syndrome" ensures that the company’s energy and resources are directed toward proven strategies and tools that truly add value. It helps in maintaining strategic clarity and ensures the team remains aligned on critical business goals, thereby driving more sustainable growth. Don’t overcomplicate your early-stage marketing strategies. Focus on a single selling proposition. For instance, ZoomInfo successfully built its business purely on outbound tactics. Finding and honing in on the company’s single greatest strength or 'superpower' can lead to substantial growth. Building a community around your product or service can significantly enhance customer engagement and retention. In-person events are a great way to improve the activity and engagement within online communities. Structured, curated communities can lead to higher customer retention and more effective peer-to-peer marketing. This helps in creating a robust, organic promotional network that can significantly impact long-term growth and customer satisfaction. Experiment with new channels and strategies but avoid overcommitting to unproven methods at the cost of what’s already working. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Intro 01:46 Introducing Eric Spett 04:21 First Deal Stories and Lessons Learned 13:05 Is Your Go-to-Market motion working? Good, Keep doing it. 23:47 Navigating Business Growth and Go-To-Market Strategies 24:11 The AI Dilemma in Business 25:41 Why LinkedIn can be A Double-Edged Sword for B2B Founders 34:00 The Power of Community Building for SaaS companies 46:14 Concluding Thoughts on Focus and Community Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “Founders, CEOs, go-to-market executives are so quick to put a lot of focus and eggs in experimental baskets when the thing that they're doing really well is still working really well. Do it and keep doing it, keep your focus.” - Eric Spett “I'm just really bullish on the need for human community and human connection.” - Eric Spett Connect with LinkedIn: https://www.linkedin.com/in/ericspett/ Website: https://scalebound.com/ Shoutouts Sangram Vajre: https://www.linkedin.com/in/sangramvajre/ Terminus Atlanta Tech Village Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Scott Albro: https://www.linkedin.com/in/scottalbro/ Scott’s Episode: https://thetransaction.substack.com/p/helping-every-founder-tell-their?r=3iae7z TOPO Everstring David Politis: https://www.linkedin.com/in/davidpolitis/ David’s Episode: https://thetransaction.substack.com/p/narrow-down-your-damn-icp-with-david?r=3iae7z Pavilion: Rob Forman: https://www.linkedin.com/in/robforman/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
1 Social Selling Secrets to Supercharge Your Sales with Sam McKenna - Ep. 48 56:31
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Play Later Play Later Lists Like LikedIt’s painfully pitiful what passes as personalized prospecting presently. However, we’ve got just the guest to help sales reps get back on the right track. Sam McKenna is the Founder of SamSales Consulting and is the foremost expert on social selling and leveraging LinkedIn to drive revenue. Sam and her team are redefining the go-to-market status quo for modern organizations through unmatched sales training and LinkedIn branding. Sam joins co-hosts Craig Rosenberg and Matt Amundson for a very fun and fascinating dive into how to improve your personalized sales messages to prospects, the secrets to successful social selling, and the best time to prospect. Plus, we share stories from some of our worst webinar fails. Also, Craig denies claims that he was in fact the heavy breather while hosting a webinar with Guy Kawasaki a decade ago and Matt reveals the truth about the size of a certain actor’s mouth. Critical Takeaways Sales reps, please take 3 seconds to THINK before sending another stinky, smelly, no-good, automated email to a prospect. If you want to stand out to them and get their attention, earn it by doing the work that none of the other reps reaching out to them won’t. Show them you know them. A simple way to stand out to decision makers at target accounts is to engage with their LinkedIn posts. However, hitting “like” does not qualify as engaging in a way that will stand out. The smart play is to comment something insightful. Prospecting during non-working hours, like weekends and evenings, can capture the attention of busy executives. Emails sent during these times can stand out because prospects are usually less overwhelmed and more likely to engage with content beyond their regular work distractions. Don’t buy a ‘great new tool’ until you know what you’re going to do with it. Figure out how to solve the problem you’re addressing before you ever get close to buying a tech solution. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Intro Sales Insights with Sam McKenna 04:38 Introducing Sam McKenna, Founder of SamSales Consulting 08:02 Announcing The New Sam McKenna Award For The Best Guest 10:13 A Particularly Titillating LinkedIn Controversy 11:44 The Airing of Our Webinar Woes 22:41 Companies Suck at Solving Problems & Try to Techstack Their Way Out of Issues 28:50 How to Run the “Been Awhile” B2B Prospecting Play using LinkedIn Sales Navigator 30:24 How to Use Social Selling in SaaS 34:40 Spearfishing for B2B Leads Using This Tactic on LinkedIn Sales Navigator 41:44 Why Putting in the Work is the Way to Wow Prospects and Customers 45:50 Why the "Show Me You Know Me" Method Works so Well for B2B Sales Reps Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ Why is it that so few people will just put in the actual work that that converts?” - Sam McKenna “ Anything that you can't automate won't be done.” - Matt Amundson Connect with Sam LinkedIn: https://www.linkedin.com/in/samsalesli/ Website: https://www.samsalesconsulting.com/ Sam’s new Podcast: https://www.samsalesconsulting.com/showmeyoukknowmeshow/ Shoutouts Hayley Hoad: https://www.linkedin.com/in/hayley-hoad-2565549/ Bobby Axelrod (Billions) Jill Rowley: https://www.linkedin.com/in/jillrowley/ Paige Tills: https://www.linkedin.com/in/paige-tills/ Joy Wilder Lybeer: https://www.linkedin.com/in/joywilderlybeer/ Gail Moody-Byrd: https://www.linkedin.com/in/gailmoodybyrd/ Adam Robinson: https://www.linkedin.com/in/retentionadam/ Adam’s episode of The Transaction: https://open.substack.com/pub/thetransaction/p/asymmetrical-marketing-and-personal Toby Carrington: https://www.linkedin.com/in/tobycarrington/ DocuSign ON24 Marketo Engagio Guy Kawasaki: https://www.linkedin.com/in/guykawasaki/ Jon Gray: https://www.linkedin.com/in/jon-d-gray/ DailyMail Article about the “LinkedIn Boobs Post”: https://www.dailymail.co.uk/news/article-14406563/linkedin-post-fury-comparing-woman-breast-size-confidence.html Bobby Axelrod/Damian Lewis Tiny Mouth Investigation: https://www.maxim.com/entertainment/damian-lewis-tiny-mouth-2016-3/ Reddit discussion of Bobby Axelrod/Damian Lewis’s tiny mouth: https://www.reddit.com/r/Billions/comments/8jcnx5/anyone_else_getting_annoyed_by_damian_lewis_tiny/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 Steak Dinners Don’t Close Deals with Maria Boulden - Ep 47 58:42
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Play Later Play Later Lists Like LikedYou’ll be hard pressed to find a more energetic and experienced sales expert than our special guest, Maria Boulden! Maria Boulden has spent over 3 decades creating and leading world-class sales teams at leading enterprise organizations like DuPont and Gartner. She brings her incredible experience in multiple verticals and truly unstoppable energy to one of the best conversations yet with co-hosts Matt Amundson and Craig Rosenberg. Maria drops some serious insight bombs in this one, including why steak dinners aren’t the deal closer that they once were, why top execs need to get down to the frontlines to talk with employees, and why ‘not broken’ is not good enough for your company to succeed. Additionally, there is some great advice in here about effectively leading change management efforts in your organization, why building personal relationships in SaaS has become so important for B2B sellers, and why you shouldn’t hold a deal signing at a Japanese gentleman’s club. Fueled by an ungodly amount of Coke Zero, Maria really brought it this episode and delivered some incredible stories, which make this a must-watch! Also, Craig tests out a new hat and Matt admits he can be bought with a burrito. Critical Takeaways Senior leaders need to be visibly and vocally present with front-line sellers periodically. This not only boosts team morale but also ensures the leader understands the day-to-day challenges and can directly impart strategic guidance. Sales teams should focus on providing value and building genuine connections rather than relying on traditional wining and dining strategies. Waiting for 'normalcy' to return so you go back to old tactics is not viable. Leaders must guide their teams to adapt to the current market conditions and be prepared for continuous change. Conducting “pre-mortem” sessions can be an effective way to anticipate potential failures and mitigate risks before executing significant strategic changes. This approach can foster an environment of proactive problem-solving and better preparedness among the team. Helping clients understand their own business better and providing insights creates stronger, more trusting client relationships. Sponsored Segment The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Intro 00:44 Craig’s Special Hat 02:35 Introducing Maria Boulden 10:39 The Challenge with Channel Partners 19:31 Brazenly Baring It All 23:03 A Quick Conversation Regarding Caffeine 23:43 Steak Dinners have Gone Stale in Sales 33:42 Stories from the Signing Party & Where NOT to Hold One 36:48 Taking a Hands-on Approach to Leadership in Sales 38:17 Unbatten the Hatches & Adapting to Market Changes 41:56 How Executives Should Engage with Their Sales Teams 50:59 Delving into some Delicious Additions to Business Dictionaries 55:30 Wrapping Up Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ It was not my aspiration that they would have world-class sales skills, it was my expectation.” - Maria Boulden “ Not broken is not good enough in this environment.” - Maria Boulden New Terms Donut Run (v): When a rep brings a box of joe and a box of donuts to meet with their distributor and ‘shoot the breeze’ for an hour. Ask Hole (n): Someone who continuously asks the same question, but never does anything with the suggestions they receive. Pre-Mortem (n): A proactive meeting held before executing a decision, campaign, etc., where the risks are clearly laid out along with what indicators should be monitored to determine real-time progress and what actions need to be taken mid-course. Connect with Maria LinkedIn: https://www.linkedin.com/in/maria-boulden-8a778b11/ Website: https://www.jsjrehoboth.com/ Shoutouts Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan’s Post: https://www.linkedin.com/posts/danielpgottlieb_good-luck-with-that-ai-theres-no-ai-on-activity-7293698734540955648-rNIz Dan’s Episode: https://open.substack.com/pub/thetransaction/p/triple-t-pov-with-dan-gottlieb?r=3iae7z Nick Toman: https://www.linkedin.com/in/nicktoman/ Nick’s Episode: https://thetransaction.substack.com/p/the-commercial-efficiency-crisis?r=3iae7z Neil Rackham Spin Selling: https://a.co/d/1FSFtS1 Mark Gustaferro: https://www.linkedin.com/in/mark-gustaferro-3894aa1a5/ Kyle Porter: https://www.linkedin.com/in/kyleporter/ Kyle’s Episode: https://thetransaction.substack.com/p/startup-stunts-and-loving-your-customers?r=3iae7z Brent Adamson: https://www.linkedin.com/in/brentadamson Brent’s Episode: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z Ted Purcell: https://www.linkedin.com/in/tedpurcell/ Bill McDermott: https://www.linkedin.com/in/billrmcdermott/ Gartner DuPont Salesforce Love the show? 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1 Overcoming Epilepsy & How to Hire with Michael King - Ep. 46 56:04
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Play Later Play Later Lists Like LikedMichael King is one of the leading marketing executive recruiters working today and is also the author of a new book, Be There When I Return, a memoir of epilepsy, love, and success. Michael joins co-hosts Craig Rosenberg and Matt Amundson to discuss his personal journey with both epilepsy and his career, along with crucial career advice for marketing leaders looking for their next roles. Michael shares how the CEO should factor into your job search, why you shouldn’t chase titles, and the state of the job market for B2B marketing executives. Also, Craig tries out a new look and Matt relives an epic beach party in Vegas. Critical Takeaways Ensure the people you hire have relevant experience at companies similar in size and stage to your own. Avoid hiring someone just because they’ve been part of a larger company’s success unless their role aligns directly with what your company needs now. Chase companies over titles. Titles shouldn't be the defining factor when considering new positions. Joining a strong, growing company should be the priority as it offers career growth opportunities in the long run. Focus on the company's potential rather than the initial title, as the ultimate career growth lies in sustainable company success. Sponsored Segment The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Intro 02:58 Introducing Michael King 04:15 Michael's New Book & Incredible Personal Journey 09:29 Recruiting Career & Success Stories 18:54 Amazing Event Marketing Anecdotes 27:44 Falling in Love with a Brand 28:33 The Importance of Relevant Experience 33:55 Chasing Titles vs. Chasing Companies 39:14 The Value of Good Companies 49:03 Epilepsy Awareness and Personal Stories Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ If you go to a good company, you will never look for a job again.” - Michael King “ For success in your career, you chase companies, you do not chase titles; you do not chase money, you chase companies” - Michael King Connect with Michael LinkedIn: https://www.linkedin.com/in/michaelking/ Website: https://kingrecruiting.net/ Book Website: https://www.michaeltking.com/ Book signing in San Francisco: https://www.bookpassage.com/event/michael-king-be-there-when-i-return-ferry-building-store Shoutouts George Wallace Maria Pergolino Will Smith & DJ Jazzy Jeff Reunion at Everstring’s Pool Party: https://youtu.be/v6-QoeusjEs?si=2CynMyahkkqG1mT8 Jessica Cross Stephanie Stacey Epstein David Mylam Dave Arnold Michael Lundgren Miles Kelly Rob Bernstein Udi Ledergor Russell Udy SuccessFactors Salesforce Broadvision Okta Coupa Siebel Gong Cresta Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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1 Fixing Your Awful Onboarding & Problematic Pipeline Progression with Katherine Andruha - Ep. 45 52:46
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Play Later Play Later Lists Like LikedEmployee churn is a serious problem that is seldom discussed, especially given how much of a detrimental impact it has on even the best companies. To help illuminate this problem and how to fix it at your organization, Katherine Andruha joins co-hosts Craig Rosenberg and Matt Amundson for a much-needed conversation filled with tips, tricks, and a few flamingos. Katherine Andruha is the Vice President of Business Development at Fivetran and has led top-performing sales teams for decades at cutting-edge SaaS companies such as Simpplr, Cloudflare, Coursera, Eightfold.ai, Anaplan, Apttus, and Aruba Networks. Katherine sheds light on where current onboarding programs fall short and shares what can be done so that employees are actually put in the best position to succeed. Additionally, Katherine dives into the importance of properly managing pipeline progression. Also, Craig recounts getting “flocked”, Matt compliments Craig’s athletic abilities, and Sam the Producer grossly mispronounces someone’s name. Critical Takeaways A comprehensive onboarding process for BDRs is critical. Make sure new BDRs aren’t making live calls until week four. This allows them to become fully comfortable with the systems, processes, and their pitches, minimizing the risk of errors and increasing their initial successes. Utilize AI tools for mock calls to simulate real-world environments. This allows BDRs to practice handling objections and refine their pitches in a risk-free environment before they contact actual leads. Incorporate various channels such as live calls, LinkedIn voice notes, and personalized videos. Ensure that new BDRs are trained to use these channels effectively as people are now more responsive to phone calls and LinkedIn interactions. Ensure that managers have a consistent checklist for onboarding and supporting BDRs. This will help maintain consistency and high standards across teams. Regularly review pipeline stages to ensure there are no stale leads. Utilize automated reminders for deals that have been stagnant for too long to push progression actively. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Intro 06:30 Introducing Katherine Andruha 11:23 Onboarding and Training Challenges 19:25 Effective Onboarding Practices for B2B SaaS Companies 29:05 The Importance of Confidence in BDRs 30:37 The Sales Manager's Role in Onboarding 33:26 Territory Ownership and AE Handover 35:15 Creating a Fun and Productive Environment as a B2B Seller 37:45 Pipeline Progression and Accountability 42:48 The Role of CMOs in Pipeline Progression 44:57 Closed Lost Analysis and Product Feedback 48:01 The Importance of Phone Calls 48:41 Using Swag to Engage Prospects Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “Know your business. It's the only way you will be taken seriously.” - Katherine Andruha “Just call the leads” - Katherine Andruha Connect with Katherine Andruha LinkedIn: https://www.linkedin.com/in/katherineandruha/ Website: https://www.fivetran.com/ Shoutouts Doug Landis: https://www.linkedin.com/in/douglandis/ Sangram Vajre: https://www.linkedin.com/in/sangramvajre/ Alan Berkson: https://www.linkedin.com/in/alanberkson/ Nooks: https://www.nooks.ai/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 The Commercial Efficiency Crisis in B2B SaaS Sales with Nick Toman - Ep. 44 57:16
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Play Later Play Later Lists Like LikedThere are more people than ever involved in deals on both the vendor side and customer side, and it’s having a massively negative impact on B2B growth. Nick Toman is the Chief Product and Transformation Officer at SBI (Sales Benchmark Index) and is the third and final co-author of The Challenger Sale we’ve had on the show. Nick brings some amazing new sales and business research to dive into with co-hosts Matt Amundson and Craig Rosenberg. Nick unveils the effect that having more sellers involved has on win rates, the three behaviors of B2B salespeople that lead to the best commercial relationships, and why actions that seem like they would slow down deals are actually the key to closing them faster. Matt sparks an interesting discussion around sales compensation and the impact it has on both the behaviors of B2B sellers and the growth of the company on the whole. Toward the end, Nick teases his new concept of 'Headway Selling,' which focuses on actually helping customers reach their goals rather than simply selling them as much useless crap as possible. Also, Craig recounts his childhood trauma of growing up a Dodgers fan in San Fransisco, Matt practices to be a court stenographer, and Sam the Producer confesses to an affinity for gnomes (?). Join our Newsletter: https://thetransaction.substack.com/ Critical Takeaways Not only have buying groups grown immensely, but the number of people working on deals with those buying groups has also exploded. There are now an average of 12 people in buying groups and 5 people involved with the sale from the vendor side. This has led to a spike in confusion for buyers and a sharp decline in win rates for salespeople. The role of CSMs (Customer Success Managers) has devolved to have an extremely broad remit that is too big for them to actually deliver on effectively. In an ideal world, the CSM role should be to use very clear signals to identify customers who are struggling with adoption or retention issues and help them solve those issues. As it stands, many CSMs provide ongoing services and end up competing with account managers to land expansion and renewal opportunities. The competition on its own is one thing, but once the business is compensating both the CSM and the AM, there’s an issue with cost and efficiency. B2B sales reps need to focus on deeply understanding and aligning with customer initiatives. Sellers should be thinking about how they can help customers grow in their own businesses and avoid roadblocks. Gaining this deeper understanding of customer needs drastically shortens sales cycles and increases deal sizes. There are 4 main archetypes of behavior for people in commercial roles: 1. Narrowing- Closing early, Closing often. 2. Provoking - Provocative insights to redirect customer thinking (AKA: Challenger). 3. Translating - Detail & data-oriented to help customers understand impact. 4. Anticipating - Help customers think through the process and future challenges. Of those 4 archetypes, the two that perform best in sales are Translating and Anticipating. The research showed that sellers exhibiting those behaviors actually closed deals more quickly and for more money than sellers using the Narrowing or Provoking behaviors. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Coming Up in this Episode... 00:40 Will the Real Nick Toman Please Stand Up 01:53 Introducing Nick Toman, Co-Author of The Challenger Sale 03:09 The Impact of The Challenger Sale in B2B Sales 13:55 Commercial Efficiency is Crippling B2B SaaS Growth 21:22 Is Sales Commision Getting out of hand for B2B Companies? 28:22 Why Don't Buyers Want to Talk to Sellers Anymore? 31:05 Key Behaviors for Successful Commercial Relationships 33:53 Why Starting Fast Is So Critical for Sales Success All Year Long 36:27 Strategies for Effective Sales Execution to Start the Fiscal Year Strong 41:08 Understanding The Four Commercial Role Archetypes & Their Impact on Deal Velocity 48:54 Customer-Centric Selling and Trust Building 53:56 Headway Selling & Delivering Real Customer Success Epic Quotes “ You’ve got to help the customer make headway and you don't want to make headwinds.” - Nick Toman “ Commercial efficiency- the yield on dollars spent in sales and marketing- has gone down 50 plus percent.” - Nick Toman “ Those who really do situate themselves in a path of helping the customer evolve their business and get things right do much better than those who are like ‘Buy this thing.’” - Nick Toman Connect with Nick Toman LinkedIn: https://www.linkedin.com/in/nicktoman/ SBI Website: https://sbigrowth.com/ Latest Research - How a Fast Start to the Year Defines Your Growth Outcomes: https://sbigrowth.com/tools-and-solutions/how_a_fast_start_defines_your_growth_outcomes Shoutouts Matt Dixon: https://thetransaction.substack.com/p/decoding-sales-indecision-with-matt?r=3iae7z Brent Adamson: https://thetransaction.substack.com/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z The End of Solution Sales - HBR Article: https://hbr.org/2012/07/the-end-of-solution-sales Dave Brock: https://thetransaction.substack.com/p/really-knowing-your-customer-with?r=3iae7z Mike Bosworth: https://www.linkedin.com/in/mikebosworth/ Neil Rackham Harvard Business Review: https://hbr.org/ Karen Freeman: https://www.linkedin.com/in/karenefreeman/ Stop Trying to Delight Your Customers - HBR Article: https://hbr.org/2010/07/stop-trying-to-delight-your-customers AJ Gandhi: https://thetransaction.substack.com/p/navigating-market-success-with-aj?r=3iae7z Vantage: https://www.vantage.sh/ Ben Schaechter: https://www.linkedin.com/in/bensign/ Marlin Equity Partners: https://www.marlinequity.com/ Gartne...…
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The Transaction
1 Identifying & Developing a Champion Buyer with Krysten Conner - Ep. 43 55:56
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Play Later Play Later Lists Like LikedThere’s a lot of confusion about how to find the champion of your product within a buying group. To help sort things out for B2B sellers, we invited Krysten Conner on the show! Krysten is an extraordinary sales coach who is hired by top SaaS revenue organizations to train their sales teams into incredible teams. Krysten has also made a number of courses available for purchase through her website and through pclub.io. Krysten joins co-hosts Matt Amundson and Craig Rosenberg to break down three ways to identify and develop strong champions within the buying group to help you close more deals. Krysten also shares the secrets to mastering multi-threading for sellers and how to maintain deal momentum with prospects so they become customers. Also, Craig shares the playbook he used to land his first girlfriend, Matt adds an “s” where he shouldn’t have, and Sam the Producer puts his foot squarely into his big mouth. Critical Takeaways There are three ways to proactively discover a champion within a prospect's buying group: 1. Do they do work asynchronous of your meeting with them? 2. Do they bring other people to follow-up meetings? 3. Do they have a point of view on the next steps? The first person to reach out or take a meeting with a seller is not necessarily the champion within that organization for your product or service. Don’t make the mistake of assuming they are the champion. Talking with you makes them a contact, not a champion, by default. “Typically” is a magic word to use in your sales calls. Buyers are very risk-averse and want to be sure they’re not doing something wrong that will get them fired. By sharing what other buyers “typically” do when it comes to things like next steps, you can give buyers peace of mind. Buyers aren’t experts at buying your product, so you need to teach them and guide them to make the right decision. This process of educating buyers and helping them avoid common pitfalls makes them feel much more comfortable. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 - Intro 03:44 - The "Let Me Help You Get this Car" Story 07:24 - Krysten’s Embarrassing Sales Stories 13:22 - Develop a Champion, Don’t Wait For Them to Show Themselves 18:39 - Examples of Asynchronous Work that Champions will Do 25:58 - Champions will Bring More People to Follow Up Sales Calls 32:36 - Craig Details how he Landed his First Girlfriend 33:35 - Who Should be Doing Asynchronous Work Within The Buying Committee 41:54 - Does Your Buyer have a Point of View on the Next Steps 44:54 - Mass Email Does Not Count as Multi-Threading 51:10 - Who a Champion Is and What They Will Do in The Buying Cycle Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ You multi-thread, by single threading.” - Krysten Conner “ When I'm sending actually any email, if it's no one's baby, it's an orphan.” - Krysten Conner Connect with Krysten Conner LinkedIn: https://www.linkedin.com/in/krystenconner/ Website: https://krystenconner.com/ Access the Free Slides Krysten Shared in this Episode: https://docs.google.com/presentation/d/1DOf9bsPh0m7WtQxwhlJfT7Yg22LkD3iukivIk0W1cOA/edit?usp=sharing Shoutouts Chris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris Orlob's Episode of The Transaction: Krysten’s Multi-Threading Course with pclub: https://go.pclub.io/multi-threading-masterclass Mark Kosoglow: https://www.linkedin.com/in/mkosoglow/ Mark Kosoglow's Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/unlocking-sales-success-creativity?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Scott Barker: https://www.linkedin.com/in/ssbarker/ Scott Barker's Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/selling-like-a-real-human-being-with?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 Positioning is a Key Pillar of SaaS Growth with Bob Wright - Ep. 42 49:35
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Play Later Play Later Lists Like LikedWithout a real point of view, your company, your product, and all of your amazing features will drift into irrelevance amidst the soothing currents of the sea of sameness we see in the state of SaaS. (Just learned about this thing called alliteration!) To help you avoid that terrible fate and aid you in developing your positioning, we are thrilled that Bob Wright, the Founder of Firebrick Consulting, joined co-hosts Craig Rosenberg and Matt Amundson on the show. As a B2B Marketing expert, Bob has helped hundreds of B2B companies define and refine their positioning over the last several decades and is one of the foremost authorities on the subject working today. In this episode, Bob illuminates the criticality of ‘selling the problem, not the solution’, why B2B positioning should be a CEO-led initiative, and the three questions that your positioning must answer for buyers. Also, Craig eats the world’s loudest piece of chocolate and Matt tries to hire another guest while live on the podcast. Critical Takeaways Sell the Problem, Not the Product. Focus on identifying and articulating the key problem your product solves for the customer. This creates urgency and relevance in the buyer's mind, making them more likely to engage with your solution. Your positioning should answer three key questions: 1. Why now? 2. How are you different? 3. Why does it matter to the customer? These answers create a compelling narrative that drives customer interest and action. Stop focusing on the features. Emphasize the broader business impact and outcomes in your B2B marketing, rather than detailed product features. This approach resonates better with executive buyers who are more concerned with strategic advantages. Shift from explaining how your product works, to inspiring the customer on why it matters to them. This makes your marketing message more compelling and memorable, driving stronger customer engagement and commitment. Sponsored Segment The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Highlights 01:56 Introducing Bob Wright, the Founder of Firebrick Consulting 07:36 Differentiate your B2B Brand or Die 17:22 Portfolio Positioning Challenges 22:00 Targeting the Right Buyers with your B2B Marketing 23:55 Expanding into New Markets 28:56 Maintaining Focus While Growing 31:06 The Importance of CEO Involvement 33:34 Effective Business Positioning Strategies 37:15 AI’s Impact on Positioning 41:52 Measuring Positioning Success for Your B2B company 42:48 Analyst Influence and Market Trends 44:51 Explaining Positioning to the Board 47:11 The Role of Storytelling in Positioning and B2B Marketing Join our Newsletter: https://thetransaction.substack.com/ Epic Quotes “Sell the problem, not the product.” - Bob Wright “ Don't waste all your go to market investments on shitty messaging.” - Bob Wright Connect with Bob LinkedIn: https://www.linkedin.com/in/findurtruegenius/ Website: https://firebrickconsulting.com/ Shoutouts AJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ Okta Microsoft Oracle SAP HPE Gartner Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 Selling like a Real Human Being with Scott Barker - Ep. 41 56:23
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Play Later Play Later Lists Like LikedSelling B2B has always been hard. The crazy buying frenzy of the ZIRP era was the exception, not the rule, so if you’re expecting the current buying climate to change any time soon, you need to readjust your perspective. Scott Barker, Partner & Co-founder of GTMfund and Host of The GTM Podcast, joins Host Craig Rosenberg and special guest-host Scott Albro to talk all things sales, venture capital, and go-to-market. Scott (Barker) shares why focus can give sales reps superpowers, the outsized impact of warm introductions when building pipeline, and how focusing on uniquely human skills can help you excel in sales. There’s also some great discussion around the importance of accountability and ownership throughout your go-to-market team. Also, Craig pitches both Scotts on launching a legal practice, Scott Albro relives the glory days of selling TOPO services, and Sam the Producer attempts to crack the case and catch the Bottle Cap Culprit. Critical Takeaways Invest time in becoming an expert in the problems you are solving for your customers. Offer valuable insights that make clients see you as invaluable. Focus on the human side of sales, including trust-building and relationship management; that’s what closes deals. Rely less on pure automation or technology and more on human connections. Sellers can emulate what works in founder-led sales by using personal testimonies about why they joined the company or how the product solved a problem for them. This can make their pitch more relatable and compelling. Warm introductions are the best way to build pipeline in what is quickly becoming an AI-dominated selling landscape Sponsored Segment The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Intro 00:26 Retreading Brent Adamson’s Maggots on a Plane Story 02:30 Introducing Scott Barker 05:10 Funny Fundraising Stories 08:33 The Importance of Humanizing Sales 12:59 Overcomplicating Pipeline Generation 16:25 The Human Side of Sales 19:39 How to Build Trust in Sales 22:08 Expertise in Sales: Lessons from TOPO 29:46 The Concept of “Opinionated Software” 34:39 Overcomplicating Pipeline Generation 38:19 The Power of Warm Introductions 43:36 Scaling Founder-Led Sales 52:59 The Value of Human Skills in the Age of AI Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ If you even have the thought of an excuse as a sales leader, as a seller, as a marketer, you're already dead in my books. It requires full and complete accountability.” - Scott Barker “ If there are things that are stopping you from doing your job, it is nobody else's problem, but your own” - Scott Barker Connect with Scott Barker LinkedIn: https://www.linkedin.com/in/ssbarker/ GTMfund Website: https://www.gtmfund.com/ GTMfund’s new fundraising announcement: https://techcrunch.com/2025/02/04/how-max-altschuler-accidentally-founded-a-vc-firm-that-just-raised-another-54m/ GTMnow Website: https://gtmnow.com/ The GTM Podcast: https://gtmnow.com/tag/podcast/ Shoutouts Brent Adamson: https://www.linkedin.com/in/brentadamson/ Brent Adamson’s Episode of The Transaction: https://open.substack.com/pub/thetransaction/p/reframing-b2b-sales-to-drive-buyer?r=3iae7z&utm_campaign=post&utm_medium=web&showWelcomeOnShare=false Max Altschuler: https://www.linkedin.com/in/maxaltschuler/ Javier Soltero: https://www.linkedin.com/in/jsoltero/ Zendesk Anthropic Microsoft Google Neil Harrington: https://www.linkedin.com/in/neildharrington/ Jim Cyb: https://www.linkedin.com/in/jimcyb/ Vinny Pazienza, AKA Vinny Paz and Vinny “The Pazmanian Devil" Pazienza Bleed For This (2016, Ben Younger) Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 Reframing B2B Sales to Drive Buyer Confidence with Brent Adamson - Ep. 40 1:00:14
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Play Later Play Later Lists Like LikedWhen your buyer isn’t confident in the decision they’re making, they will choose not to decide. Meaning, that you’re not going to close that deal, which is a serious problem in B2B. To help solve that problem, we’re thrilled to welcome Brent Adamson, the co-author of The Challenger Sale and renowned sales speaker, to the show. Brent joins hosts Matt Amundson and Craig Rosenberg to discuss the crucial sales topics in his new upcoming book, The Framemaking Sale . They get into the problem with value-selling, why sellers need to teach buyers how to buy with confidence, and where thought leadership is falling short in today’s environment. Also, Craig pitches an idea for a radical new podcast and Matt cuts to the front of the line to call dibs. Critical Takeaways Focus more on building customer confidence in their own decision-making abilities rather than just showcasing the value of your product. If customers are reluctant or unsure, they will likely delay or avoid purchasing altogether. Bring implementation and customer success representatives into pre-sale discussions. This helps reassure the customer that post-sale support will be robust and demonstrates your commitment to their success. Instead of just showcasing customer success stories, position them as a tool to show customers how to buy so that new customers understand the buying process and pitfalls to avoid. This gives prospects practical advice and increases their confidence in making a complex decision. Optimize your sales process to lose deals quickly. If a deal is likely to be lost, aim to lose early rather than late. This saves your sales team time, resources, and focus for more promising opportunities. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 - Trailer 01:25 - Introducing Brent Adamson 03:51 - I’m Tired of these MFing Maggots on this MFing Plane 10:08 - The Impact of Buyers’ Low Confidence in Themselves 18:42 - Buyers Don’t Know How to Buy 23:44 - Implementing a Objectives, Tactics, Results Approach to Sales 30:49 - The Problem with Replicating Successful Sellers 36:26 - Thought Leadership & Content Marketing’s Role in Building Confidence 40:49 - How to Building Customer Confidence 45:16 - The Role of Founders in Sales 51:39 - Wrap Up Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “Solve for customer’s confidence in themselves” - Brent Adamson “ It's not that I'm selling badly, it's that customers are buying badly.” - Brent Adamson Connect with LinkedIn: https://www.linkedin.com/in/brentadamson Website: https://www.brentadamson.net/ A to B Insights Website: https://atobinsight.com/ Maggots on a Plane Video: https://youtu.be/BFp30CkVcLo?si=aDSKIeQOTfyt9IZ5 Shoutouts Karl Schmidt: https://www.linkedin.com/in/karl-schmidt-q/ Bryan Smith: https://www.linkedin.com/in/bryankeithsmith/ Tyler Harnish: https://www.linkedin.com/in/tylerharnish/ Marc Benioff: https://www.linkedin.com/in/marcbenioff/ Sense-making for Sales in HBR: https://hbr.org/2022/01/sensemaking-for-sales Matt Dixon: https://www.linkedin.com/in/matthewxdixon/ Stephen Powell: https://www.linkedin.com/in/stephen-powell-06996785/ Kevin Hendrick: https://www.linkedin.com/in/kevinhendrick/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 Leading in Your Own Voice with Dia Bondi - Ep. 39 52:32
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Play Later Play Later Lists Like LikedWhen you can tell your story in a compelling, confident way, you can change the lens through which everyone views you, your accomplishments, and your potential. Dia Bondi, a TEDx speaker, author of Ask Like An Auctioneer , and executive coach, joins Hosts Craig Rosenberg and Matt Amundson for an exceedingly energetic and entertaining conversation focused on communicating effectively as a leader. In between some fun tangents, they dig into how to uncover and craft your origin story to tell a more compelling narrative, why doing live demos on stage needs to go the way of the dodo, and how to raise more funding without a pitch deck. They also discuss their favorite examples of leaders who are actually doing this well and showing the world who they really are. Strap in for a fun and informative fifty-two minutes that every aspiring leader needs to hear (or watch if you’re on Spotify or YouTube). Also, Matt mixes up 1960s movie characters named Felix and Craig channels his inner Sully as he desperately attempts to land multiple planes. Join our Newsletter: https://thetransaction.substack.com/ Critical Takeaways When someone asks you who you are, don’t rifle through the bullets of your resume. Instead, tell them the narrative of your origin story. Include the core things that drive you, the context around why you set out to do X, and who you really are. Speaking on stage is too expensive for you to have a live demo of your product that doesn’t work. It’s much better to have a pre-recorded demo for your presentation and then give people an opportunity to interact with a live demo at your booth where things are lower stakes if the product fails. Founders need to realize when to hand off the tactical duties in their all-hands meetings, such as being the emcee or running a slide deck. Your team needs you to show up at the status that matches the role that people need you to play in the world. All-hands meetings are extremely expensive, especially the ones that are run poorly and time-intensive. You need to allocate your team’s time carefully based on what is most important to the company’s mission, so make sure not to squander that precious time. Being a compelling communicator is not about being perfectly polished, it’s about staying true to yourself and adapting your natural approach to each context while maintaining authenticity. Sponsored Segment The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 - Intro 00:20 - Craig comes Straight Outta Compton 00:58 - Fun Facts about Dia Bondi, Matt, & Softball 04:09 - Introducing Dia Bondi 08:20 - The Impact of Establishing Your Voice 12:13 - What is Founder Unrest & When Does It Show Up? 15:19 - How Founders can Find Their Own Voice & Unlock Their Origin Story 20:42 - Why Understanding How to Tell Your Origin Story Matters 31:12 - Dump the Live Demos from your Presentations 33:15 - Wait, How Expensive are All-Hands Meetings? 38:20 - Two Big Misconceptions about Communication 43:44 - Examples of Leaders with Great Perspectives & Well-Developed Voices 50:04 - Craig Compliments Sam for Displaying Basic Competence 50:24 - Wrapping Up Epic Quotes “ Founders are always going into conversations that are bigger than their britches. That's kind of like a job requirement.” - Dia Bondi “ To win and to differentiate today, we need the founder to reach trusted superstar status as fast as possible.” - Craig Rosenberg “ I think of founder voice as something you lend to your venture.” - Dia Bondi Connect with Dia LinkedIn: https://www.linkedin.com/in/dia-bondi/ Website: https://www.diabondi.com/ Dia’s TED Talk: https://youtu.be/mFtHKTgyjyU?si=oElL9kWENAiSMary Ask Like An Auctioneer (Book): https://www.asklikeanauctioneer.com/ Dia’s Resource Library: https://www.diabondi.com/resources New Terms: Buttwing (v): To guesstimate. See Also: Ballpark Shoutouts Claire Sua-Amundson: https://uclabruins.com/news/2013/4/17/208207255 Claire Pitching to Dan Le Batard: https://youtu.be/o-HM5Sm5omA?si=3yzu1TtT_tD5mUyq Funny Article about Claire and Matt: https://vault.si.com/vault/2005/06/06/-hitting-the-big-time Dan Le Batard: https://lebatardaf.com/ The Odd Couple (1970-1975) Howard Schultz: https://www.linkedin.com/in/howardschultz/ Howard Schultz Interview on Acquired: https://youtu.be/A0fvX-wV70Y?si=-Ljn1jqTYP5aGEaR Starbucks: https://www.starbucks.com/ Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ Jensen Huang Interview on Acquired: https://youtu.be/y6NfxiemvHg?si=bfv8w-1wgTZk5l6A Nvidia: https://www.nvidia.com/en-us/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ David Solomon: https://www.linkedin.com/in/david-m-solomon/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 Unlocking the Cheat Code for Go To Market with Justin Gray - Ep. 38 1:06:14
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Play Later Play Later Lists Like LikedJustin Gray, author of the brand new The Go-to-Market Cheat Code and Co-Founder of In Revenue Capital joins Hosts Matt Amundson and Craig Rosenberg to share how to build more effective and efficient B2B partnership programs, why nothing seems to be working in marketing, and his cheat codes to go-to-market success in B2B. Justin explains how and why LeadMD evolved from being a competitor to building an extremely strong partnership with Marketo. There’s also a great discussion about what VCs and other investors look for in founders when investing in startups and how this has changed in recent history. Also, Matt vehemently opposes accusations of being hyperbolic and Craig recants on one of his ill-concieved New Years resolutions. Critical Takeaways The success of any partner progam depends first and foremost on executive alignment. Without buy-in from leadership, 99% of B2B partnerships will fail. No matter how good your content may be, you still have to earn the right and access to get your content in front of your target audience by building strong relationships. Stop looking for copy and paste playbooks to use that are being used by everyone else in the market. If you don’t you’ll just be adding your content and brand to the endless pile of lifeless, gray ooze of things that get ignored. Take a risk and you’ll at least have a chance of sticking out. Any partner motion begins with building a relationship with one person. Find the right people to focus on and start one at a time. This is a much quicker way to build real relationships and trust than trying to boil the ocean and make a play for everyone at once. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Introducing Justin Gray 00:50 The Origin Story of LeadMD and how they Partnered with Marketo 09:55 The Go-To-Market Cheat Code Book 16:47 Craig makes fun of Justin’s Office 18:12 Lessons on Relationships from The Wild West of the Payment Processing Industry 30:26 The Cycle of Innovation and Imitation 32:09 The Importance of Knowing Your Buyer 40:34 What Venture Capital looks for in Founders 46:50 Building Effective Partnerships 1:05:02 18th Book Plug of the Episode Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ What's working is what has always worked which is trusted relationships” - Justin Gray “Innovators look for ideas” - Craig Rosenberg Connect with Justin LinkedIn: https://www.linkedin.com/in/inrevenue/ The Go-to-Market Cheat Code (Book): https://inrevenue.capital/cheat-code/ Order The Go-to-Market Cheat Code on Amazon: https://amzn.to/4hjtrbA In Revenue Capital Website: https://inrevenue.capital/ The GTM Cheat Code (Podcast): https://inrevenue.capital/insights/?article_category=podcast Shoutouts Essentials/Fear of God Clothing: https://fearofgod.com/ Focus MAAS Impact Chris Selland: https://www.linkedin.com/in/cselland/ LeadMD Marketo Bill Binch: https://www.linkedin.com/in/bill-binch-302a4a2/ Margaret Hoogerbeets: https://www.linkedin.com/in/mhoogerbeets/ Amy Guarino: https://www.linkedin.com/in/amyguarino/ Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Scottsdale Princess: https://www.scottsdaleprincess.com/ Josh Wagner: https://www.linkedin.com/in/joshwagneraz/ Jon Miller: https://www.linkedin.com/in/jonmiller2/ Jon Miller’s Post about the Tragedy of the Commons in Marketing: https://www.linkedin.com/posts/jonmiller2_mpb2b-b2bmarketing-marketingautomation-activity-7262460572032483328-hs0J ? Dirty Money, Season 1, Episode 2: https://www.netflix.com/us/title/80118100?s=i&trkid=258593161&vlang=en Bessemer: https://www.bvp.com Nick Mehta: https://www.linkedin.com/in/nickmehta/ Marc Beniof: https://www.linkedin.com/in/marcbenioff/ Founder’s Fund: https://foundersfund.com/ Asher Mathew: https://www.linkedin.com/in/ashermathew/ AWS Marketplace: https://aws.amazon.com/marketplace Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 Helping Every Startup Founder Tell Their Story with Scott Albro - The Transaction - Ep. 37 1:03:21
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Play Later Play Later Lists Like LikedEvery Founder has a story to tell and by telling that story in a compelling way, they can give their company an outsized advantage and the leg up they need in order to grow. The founder of multiple companies and a veritable thought leader in his own right, Scott Albro, joins Hosts Craig Rosenberg and Matt Amundson, for a rollicking romp through the big AI questions now getting asked, the fundamentals for building a successful founder brand, and how to create high-quality content that is worthy of your buyers’ time and attention. The crew dives into an intriguing debate over whether AI Co-Pilots or multitudinous AI Agents will win out in the future as AI is integrated into more go-to-market jobs and processes. Scott shares his three-part framework for helping founders tell compelling stories and everyone, including Sam, shares their favorite examples of successful founder brands. Also, Craig is complimented on his militaristic sleeping abilities and Matt begins the long journey to recovery by admitting to his reprehensible road rage. Sign up for our Newsletter: https://thetransaction.substack.com/ Critical Takeaways For the love of god, please prioritize quality ahead of quantity. For example, your sales and marketing teams should focus on producing high-quality content and interactions that resonate with target customers, rather than just attempting to increase touchpoints indiscriminately. Just because you can, definitely does not mean that you should (You should have learned this from Jurassic Park). Publishing quality content consistently is critical for anyone building a following on social media platforms. A good cadence for growth on most platforms is posting three times a week. This helps you stay on top of your audience’s feed and top of mind for buyers. Create content in the medium and format that is most comfortable for you. Whether it’s writing, video, or audio, the point is to not make the content production process more painful for you. The three types of stories that Scott recommends founders telling are: 1. How well you understand customer pain points, their priorities, and how to solve their problem. 2. How the market will change and how to navigate it. 3. Your personal journey. Using AI to write crappy, clearly fake comments on LinkedIn posts from contacts within your target accounts will cause major damage to your brand. Automated comments on LinkedIn are extremely easy to spot and Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 - Walking Through a Winter Wonderland 03:23 - Introducing Scott Albro 10:51 - AI Adoption is Taking Us Down the Wrong Path 13:20 - The Important AI Debates Happening Today 16:03 - Where AI Agents & Co-Pilots Fit into Go-To-Market 27:20 - Using AI on LinkedIn 37:47 - Creating Quality Content 47:29 - Scott's Framework for Which Story Founders Want To Tell 50:22 - Examples of The Best Founder Brands 57:21 - The Impact of Scott's Shoe Game on the Market Epic Quotes “ AI feels like a market where we are going to experiment our way into the right use cases. Because they're not obvious” - Scott Albro “Every founder has a story to tell. Otherwise they wouldn't have started a company.” - Scott Albro Connect with Scott Albro LinkedIn: https://www.linkedin.com/in/scottalbro/ Shoutouts Chris Orlob: https://www.linkedin.com/in/chrisorlob/ Chris Orlob’s Episode of The Transaction: https://substack.com/@thetransaction/note/p-143505807?utm_source=notes-share-action&r=3iae7z Matt Dixon: https://www.linkedin.com/in/mattdixon/ Matt Dixon’s Episode of The Transaction: https://substack.com/@thetransaction/note/p-153859244?utm_source=notes-share-action&r=3iae7z David Politis: https://www.linkedin.com/in/davidpolitis/ David Politis’ Episode of The Transaction: https://substack.com/@thetransaction/note/p-152597131?utm_source=notes-share-action&r=3iae7z John M. Jack: https://www.linkedin.com/in/johnmjack/ Bland.ai: https://www.bland.ai/ Dan Gottlieb: https://www.linkedin.com/in/danielpgottlieb/ Dan Gottlieb’s episode of The Transaction: https://substack.com/@thetransaction/note/p-149757433?utm_source=notes-share-action&r=3iae7z Gartner: https://www.gartner.com/en AI Adoption Study from Scale Venture Partners: https://www.scalevp.com/insights/ai-gtm-flash-survey-how-marketing-teams-are-actually-using-ai/ Regie.ai: https://www.regie.ai/ Outreach: https://www.outreach.io/ Salesloft: https://www.salesloft.com/ Srinath Sridhar: https://www.linkedin.com/in/sridharsrinath/ Jensen Huang: https://www.linkedin.com/in/jenhsunhuang/ Marc Beniof: https://www.linkedin.com/in/marcbenioff/ Tobias Lütke: https://www.linkedin.com/in/tobiaslutke/ Shopify: https://www.shopify.com/ ServiceTitan: https://www.servicetitan.com/ Adam Robinson: https://www.linkedin.com/in/retentionadam/ RB2B: https://www.rb2b.com/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 THE Blueprint for B2B Go-To-Market with Adam B. Needles - The Transaction - Ep. 36 1:00:39
1:00:39 Play Later Play Later Lists Like Liked1:00:39
Play Later Play Later Lists Like LikedWhat is your GTM strategy built on? The cool new motion that's popular this minute? Tons of research on users? Well, it should be built from a blueprint and this guest just so happens to know how to create said blueprint. Adam B. Needles, the CEO of ANNUITAS, joins Craig Rosenberg and Matt Amundson for a barn burner of an episode that starts off with Adam’s seriously spicy take that the CMO’s role is a major part of the problem in the current B2B buying experience (Sounds like someone got into the Commsor hot sauces) . After unpacking that hot tamale, Adam shares some great insights on the three parts to setting up and monitoring your Go-To-Market Blueprint, why you need to educate your board on how you go to market, and what buyers actually want from sellers during their buying journey. As if that wasn’t enough to include in this edition, Adam also drops a great nugget that AI can’t cover up your poor GTM Strategy. Pretty sure the B. in Adam’s name stands for B2B Badass or something like that based on this episode. (Yes, that was corny and stupid and yes, a human, albeit not a very bright one, wrote that) Also, Craig reminisces about his viral, rebellious past and Matt sits in a corner and cries at the downfall of his fiefdom. Critical Takeaways The three core components of a go-to-market blueprint are understanding the buyer's journey, identifying all relevant decision-making stakeholders, and grasping their content consumption habits. This helps in synchronizing b2b marketing and sales efforts to ensure value-added interactions at every touchpoint. Every b2b marketing touchpoint should focus on adding value to the prospect's journey. That means every email, meeting, and piece of content prospects receive serves a purpose and helps them arrive at a quality decision faster. Don’t treat your go-to-market plan as if it’s set in stone. You should regularly meet with crossfunctional leaders to review the gtm blueprint, examine your performance against that blueprint, and update your go to market strategy based on new data and insights. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 - Freeing The Funnelholic 07:18 - The Problematic Role of the Chief Marketing Officer for B2B companies 20:52 - Creating a Value-Added Demand Motion for Buyers 34:11 - Building Your Go-To-Market Blueprint 40:47 - How to Get Your Board… On Board 49:53 - Daring to Peek Outside of the Tech Industry 56:17 - Your B2B Go-To-Market Playbook Needs a Playbook Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “ I don't think that AI is the solution to your bad go to market.” - Adam B. Needles “It's not about funnel management. It's really about just understanding where someone is in the journey.” - Adam B. Needles “If you don't have a clear sense of who owns what by stage, then nobody owns it.” - Adam B. Needles “ The new playbook is to have a playbook.” - Matt Amundson “ We talked about the CEO and COO, actually, now, the biggest education point for this change is board level.” - Craig Rosenberg Connect with Adam LinkedIn: https://www.linkedin.com/in/abneedles/ Website: https://www.annuitas.com/ Shoutouts Carlos Hidalgo: https://www.linkedin.com/in/carlosahidalgo/ Jason Stewart: https://www.linkedin.com/in/jasonhstewart/ Monotype Ninan Chacko: https://www.linkedin.com/in/ninan-chacko-54b527/ Bob Seiler: https://www.linkedin.com/in/robertjseiler/ Schneider Electric Procter and Gamble QA Symphony Forrester Gartner Evan Kent: https://www.linkedin.com/in/evankent/ Salesloft Outreach HubSpot Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 Your Buyers Are People Too with Mini Peiris - The Transaction - Ep. 35 56:41
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Play Later Play Later Lists Like LikedIf people are the ones buying software, then it’s probably important that your brand appeals to those people. Fresh off a successful Dreamforce, Mini Peiris, the Chief Market Officer of Nintex, joins co-hosts Craig Rosenberg and Matt Amundson for an examination of how a brand should make buyers feel about themselves, the problems they face, and the solution provided. Mini also gets into when is the best time to ask customers for referrals, why playing nice with sales is key to being a successful Chief Marketing Officer, and how to reinforce a brand internally so that every customer touchpoint and interaction feels right. In a seeming first for the show, the conversation takes us past the point of transaction to look at the CMO’s role in the customer’s post-sale experience. Also, Craig reveals his favorite source of apple fritters and Matt says something that is very succinct and to the point. Critical Takeaways Even though you’re in B2B, it's still humans making the purchasing decisions. Focus on the people behind the accounts, the problems they face, and what their goals are to create more impactful B2B marketing messaging. Marketing’s job isn’t over when the customer signs on the line which is dotted. It’s crucial to continue engaging with customers post-transaction to ensure they derive value from your product and can become powerful and vocal advocates of your brand. The CEO is critical in developing and or pivoting the internal brand and culture of a company. Understanding them and getting their buy in and support is step number one for any Chief Marketing Officer looking to establish or adjust their company's brand. Great B2B marketing and storytelling can gloss over a product’s inferiorities and position a brand as the category leader. If you can articulate the customers’ problem and your solution better than your competitors, your brand will win, giving you time and resources to then shore up product deficiencies. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 - Live from San Fran, It’s Matturday Night Live 04:10 - What Makes a Great CMO and B2B marketing leader 07:34 - Don’t Forget that People Buy Software in B2B 13:38 - How Mini Built a Customer Community with Donuts 18:57 - Developing Your B2B Brand’s Core Identity 21:59 - The CEO’s Influence on Brand & Culture 27:19 - Examples of Great B2B Brands 32:34 - The CMO’s Role in The Post-Transaction Customer Experience 40:19 - How Execs Buy B2B Software Today: Friends over Funnels Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “You have to know yourself before you can go tell others your story.” - Mini Peiris “ Nobody buys anything these days without calling up three of their friends. So if a friend's already making the intro, cause they took the leap, you have a better shot.” - Mini Peiris Connect with Mini LinkedIn: https://www.linkedin.com/in/mini8ture/ Website: https://www.nintex.com/ Shoutouts Matthew Luhn: https://www.linkedin.com/in/matthew-luhn-52a40629/ Geraldine McGinty: https://www.linkedin.com/in/geraldinemcgintymd/ Drift: https://www.salesloft.com/platform/drift HubSpot: https://www.salesloft.com/platform/drift Zendesk: https://www.zendesk.com/ Rippling: https://www.rippling.com/ Lifetime Fitness: https://www.linkedin.com/company/lifetimeinc/ Qualtrics: https://www.qualtrics.com/ Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 Narrow Down Your Damn ICP with David Politis - The Transaction - Ep. 34 50:28
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Play Later Play Later Lists Like LikedWhat would you say if your CEO told you they wanted to speak with 100 customers in 100 days? That’s exactly what our guest, David Politis, did and he still thinks it’s one of the best things he’s done in his career. David, the Founder and Executive Chairman of BetterCloud and Host of Not Another CEO Podcast , joins co-hosts Craig Rosenberg and Matt Amundson for a must-listen episode for founders, CEOs, and B2B execs. David explains why having a smaller TAM (Total Addressable Market) is actually good for smaller or newer-stage companies. There are also great discussions about when landing a big customer can be a bad thing for your company’s roadmap, why meeting with customers is so critically important for leaders, and how to stand out as a sales rep to book meetings with decision-makers at ideal customers. Also, Matt gets a very meaningful head nod and Craig is called an inspiration, a high that his ego may be chasing for a long time. Critical Takeaways Narrow down both your ideal customer profile and your ideal buyer persona. While this may seem counterintuitive, the larger your TAM (Total Addressable Market), the slower your company will grow. When you try to go after too many customer profiles and buyer personas, your budget, time, and effort get dispersed across them and it’s harder to gain a real foothold in any niche from which you can later expand beyond. When you focus on one key buyer persona within one ICP (Ideal Customer Profile), you can delve deeper into understanding not only how they will use your product, but also what your product actually means to them. For example, when Matt was working in marketing automation, he was able to understand that his product gave buyers a seat at the revenue table and made their jobs easier. Especially for early-stage startups, there is nothing that is more valuable than talking with your customers. Those conversations function as critical data points that you can use in every aspect of the company, from writing messaging and crafting sales narratives to building new features and raising funds. Proving to people that you and your email or message aren’t just automated is harder than ever now, so to really cut through the noise and get noticed, you need to do things that can’t be automated. In-person and handwritten things work well for this. Sponsored Segment Ringmaster Conversational Marketing - The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts. Learn more at https://ringmaster.com/ Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 When Craig Met David, His Forever-23-ish Wunderkind 06:07 Stop Supersizing Your TAM, Narrow Down Your ICP 09:34 The Dangers of Landing a Whale Client & How To Handle Your Big Fish 18:11 Which Comes First, The Product or The Persona? 23:19 Why a CEO Would Want to Meet 100 Customers in 100 Days 30:48 Sales Reps Need To Take The Opposite Approach to Automation 41:50 Creating Memorable Moments for Prospects & Customers Through Events 47:50 Matt Provides His Expert Critique of David’s Art Exhibition Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “In the early stage, every customer conversation is gold.” - David Politis “There's nothing that you can do that's as valuable as meeting customers, once you're an executive.” - Matt Amundson Connect with David LinkedIn: https://www.linkedin.com/in/davidpolitis/ BetterCloud Website: https://www.bettercloud.com/ Work-Bench Website: https://www.work-bench.com/ Not Another CEO Podcast: https://podcast.notanotherceo.com/ The StartUp Founder Survival Guide: https://www.linkedin.com/posts/davidpolitis_startup-founder-survival-guide-david-politis-activity-7158455968194875393-QVdh Shoutouts Chris Degnan: https://www.linkedin.com/in/chris-degnan-524470/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Phil Fernandez: https://www.linkedin.com/in/phil-fernandez-6902881/ Jon Miller: https://www.linkedin.com/in/jonmiller2/ Ryan Azus: https://www.linkedin.com/in/ryanazus/ Megan Eisenberg: https://www.linkedin.com/in/meageneisenberg/ Warburg Pincus: https://warburgpincus.com/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 Startup Stunts & Loving Your Customers with Kyle Porter - The Transaction - Ep. 33 58:19
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Play Later Play Later Lists Like LikedHow do you steal the spotlight from Marc Benioff at Dreamforce? By hiring a Benioff impersonator. Yes, Kyle Porter and the Salesloft team ACTUALLY did that. But they didn’t stop there… Joining co-hosts Matt Amundson and Craig Rosenberg to chat about the amazing stunts pulled in the early days of Salesloft and how to build a healthy company culture is Kyle Porter himself, the Founder and Board Chair of Salesloft. Beyond bringing a Benioff doppelganger to Dreamforce, Kyle shares some brilliant plays his team used to drive brand awareness and become the biggest story at their competitor’s conference. Kyle also dives into how he built a loving culture within Salesloft and how that loving culture was extended to and felt by their customers. Also, Craig provides a gripping tale about his experience with an elevator and Matt sets the record straight on whether a presentation he gave was sweaty or swear-y. Sign up for our Newsletter: https://thetransaction.substack.com/ Critical Takeaways When you really love your customers and they can actually feel that love, they are willing to go to bat for you and your company. Because Matt felt that Kyle loved him-as a customer-he would defend and promote Salesloft when others were defending or promoting a competitor. Building a strong company culture is more important than ever. It should be built on love–in a platonic way–for the members of your organization. A healthy organizational culture translates to better team dynamics, productivity, and ultimately, better customer interactions and satisfaction. Dare to be different, especially when it comes to events. People will only really remember 1-2 things from an event, so it’s critical to make that shortlist. A bigger booth doesn’t necessarily make you more memorable. Most event booths zig, so find a way to zag, even if it means doing something other than a booth (Sorry if that one hit too close to home). Sponsored Segment This episode is presented by Ringmaster Conversational Marketing, the go-to branded podcast team. To discover how your company can leverage B2B podcasts to deliver outsized ROI, visit ringmaster.com. Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Introducing Kyle Porter! 08:25 Awesome SaaS Stunts from the Salesloft Team 26:00 The Importance of Organizational Culture and Leadership 30:18 Loving Your Customers 32:54 Building a Community & Leveraging Customer Advocacy 44:28 How to Build a GREAT Sales Deck and Engage with Key Decision Makers 50:36 The Impact of Kyle’s Brand as a Founder Epic Quotes “We're going to continually love and serve our customers and our people better than anyone else. And when you care more than anyone else, you're going to win ultimately.” - Kyle Porter “When a customer bought SalesLoft, I had the mentality that they had just saved my life and I was going to treat them as such” - Kyle Porter “Taking care of your employees Actually helps you take care of your customers” - Matt Amundson Connect with Kyle LinkedIn: https://www.linkedin.com/in/kyleporter/ Website: https://www.salesloft.com/ Kyle’s post about the Marc Benioff Impersonation (with pictures): https://www.linkedin.com/pulse/20141022175506-2446560-how-we-impersonated-the-salesforce-com-ceo-for-one-of-the-best-marketing-hacks-at-dreamforce/ The Puppy Party for #Unleash17: https://x.com/Salesloft/status/872167164123459584 Shoutouts Jon Birdsong: https://www.linkedin.com/in/birdsong/ Mike Damphousse: https://www.linkedin.com/in/damphoux/ Behind the Cloud by Marc Benioff: https://amzn.to/3CE8WXS AJ Gandhi: https://www.linkedin.com/in/anjaigandhi/ AJ Gandhi’s episode of The Transaction: https://thetransactionpod.com/episodes/navigating-market-success-with-aj-gandhi-the-transaction-ep-26 Cam Melson: https://www.linkedin.com/in/cameronmelson/ Anthony Zhang: https://www.linkedin.com/in/theanthonyzhang/ Tami McQueen: https://www.linkedin.com/in/tamimcqueen/ Business Insider Article about Benioff for President Campaign: https://www.businessinsider.com/dreamforce-2015-adrian-grenier-wants-to-be-marc-benioffs-running-mate-2015-9 Sean Kester: https://www.linkedin.com/in/theseankester/ Mac Reddin: https://www.linkedin.com/in/mac-reddin/ Kevin O’Malley: https://www.linkedin.com/in/omalley/ Peter Kazanjy: https://www.linkedin.com/in/kazanjy/ Carolyn Feibleman: https://www.linkedin.com/in/carolynfeibleman/ Nick Mehta: https://www.linkedin.com/in/nickmehta/ Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ Trish Bertuzzi: https://www.linkedin.com/in/trishbertuzzi/ Steve Richard: https://www.linkedin.com/in/saleskickoffspeaker/ John Barrows: https://www.linkedin.com/in/johnbarrows/ Jason M. Lemkin: https://www.linkedin.com/in/jasonmlemkin/ Mark Suster: https://www.linkedin.com/in/marksuster/ Brad Feld: https://www.linkedin.com/in/bfeld/ Ken Krogue: https://www.linkedin.com/in/kenkrogue/ Love the show? Give us a shoutout on LinkedIn and tell what you loved!…
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The Transaction
1 Defining Metrics & Aligning Goals Between Sales & Marketing with Tricia Gellman - Ep 32 45:35
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Play Later Play Later Lists Like LikedWhat does a sales opportunity mean to you? Would the rest of your company give the same answer? Probably not. But not to fear, GTM leader, because Tricia Gellman, the Chief Marketing Officer of Box joins hosts Matt Amundson and Craig Rosenberg to explain how to fix the cracks between sales and marketing in B2B. Tricia outlines the importance of having shared goals across B2B sales and marketing teams, why defining terms clearly is so critical, and what it’s like for those selling AI tools to B2B buyers. Also, Craig recounts his time spent hanging out with reps at Dreamforce and Matt gushes about the events TOPO used to run. Critical Takeaways A crucial component in driving B2B sales and marketing alignment is using the same metrics and dashboards to accomplish shared goals. Consistency and agreement on these metrics will help streamline the goal-setting process, reduce friction, and ensure everyone is working towards the same company objectives. Clearly define what constitutes an opportunity and different stages within the pipeline. Aligning these definitions across marketing and sales will prevent discrepancies and confusion, leading to more accurate performance tracking and reporting. Invest in brand building. A strong B2B brand is essential for long-term success and helps in making conversations happen at the C-suite level. This investment continues to pay off by fostering word-of-mouth recommendations and creating a lasting impression in the minds of decision-makers. Building a customer or peer community, especially around high-level executives and key decision-makers, can significantly enhance your brand's reach and credibility. Hosting events and creating opportunities for peer networking add tremendous value and deepen customer loyalty. Sponsored Segment This episode is presented by Ringmaster Conversational Marketing, the go-to branded podcast team. To discover how your company can leverage B2B podcasts to deliver outsized ROI, visit ringmaster.com. Interested in becoming a sponsor of The Transaction? Contact thetransaction@samguertin.com Chapters 00:00 Tricia's Italy Trip & Career Advice 03:08 Overcoming the Challenges of a B2B Chief Marketing Officer 04:51 Managing Pipeline in the Current SaaS Environment 08:56 How to Align B2B Marketing and Sales Teams 23:26 Aligning Incentives Across Go-To-Market Teams 24:01 Defining Opportunities and Meetings 25:18 Adapting to AI in B2B Sales 27:13 Transitioning to a New CMO Role in a B2B company 32:22 Building a Customer Community and Product Alignment Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “Saying you can't do it because you don't have the data is just a cop out.” - Tricia Gellman “Everybody works to their goals. Whatever the incentive is, that's what people work towards.” - Tricia Gellman “One of the key roles of leadership across sales and marketing is really being clear on who are we going after? Why are we going after it? And then, how are we going to go after it?” - Tricia Gellman Connect with Tricia Gellman LinkedIn: https://www.linkedin.com/in/gellmansfmarketing/ Website: https://www.box.com/home Shoutouts Mini Peiris: https://www.linkedin.com/in/mini8ture/ Maria Pergolino: https://www.linkedin.com/in/mariapergolino/ Sydney Sloan: https://www.linkedin.com/in/sydsloan/ Ted Purcell: https://www.linkedin.com/in/tedpurcell/ Latané Conant: https://www.linkedin.com/in/latane-conant/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 AI Idea Starters, B2B Influencers, & Organic LinkedIn Tactics with Dave Gerhardt - Ep 31 53:03
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Play Later Play Later Lists Like LikedWow, Season Two is kicking off strong with this incredible episode with Dave Gerhardt, an astonishing marketer and the Founder & CEO of Exit Five. Dave joins Craig Rosenberg and Matt Amundson to share how he approaches using AI for B2B marketing, why LinkedIn influencers present a huge opportunity for B2B brands, and the outsized impact that building a strong Founder Brand can have for startups. Also, Matt shares his innermost feelings about Dave and Craig examines his own facial hair. Critical Takeaways Social media should be treated as the primary marketing channel for B2B SaaS brands, not just a supplementary piece of your strategy. AI tools are best used as an “idea starter” to get your writing going, rather than relying on the artificial intelligence to do the actual writing itself. Working with micro-influencers who have a strong, niche following can be highly effective in B2B SaaS. To see good results, it's important to create offers and content that align with what their audience wants to see. Narrowing down your Ideal Customer Profile (ICP) is crucial for B2B growth. Starting with a more specific market allows for easier traction and learning which you can later apply more broadly as your company scales. Sponsored Segment New Sponsor coming soon! Interested in becoming a sponsor of The Transaction? Contact transactionpod@samguertin.com Chapters 00:00 Matt provides a safe space for Dave 02:06 Discussing Founder Brand and B2B Marketing Strategies 04:45 The Power of Personal Branding and Social Media for Startups 09:42 AI Tools in B2B Marketing: Opportunities and Misconceptions 20:00 B2B Influencers and LinkedIn Strategies for SaaS companies 26:19 Understanding the Full Funnel in B2B Marketing 27:26 The Power of LinkedIn and Social Media 31:18 Narrowing Down Your Ideal Customer Profile (ICP) 37:03 The Story Behind Drift's Success 40:00 Building a Strong B2B Brand and Content Strategy 46:56 An In-depth Review of Craig’s Facial Hair Sign up for our Newsletter: https://thetransaction.substack.com/ Epic Quotes “Social media is the way marketing happens in our lives today.” - Dave Gerhardt “I use [AI] a lot as my writing partner, you can't really have writer's block anymore because you kind of always have something to get going” - Dave Gerhardt “I love you.” - Matt Amundson Connect with Dave LinkedIn: https://www.linkedin.com/in/davegerhardt/ Website: https://www.exitfive.com/ Podcast: https://media.exitfive.com/podcast Shoutouts Adam Robinson: https://www.linkedin.com/in/retentionadam/ Bland AI: https://www.bland.ai/ HeyGen: https://www.heygen.com/ Danielle Messler: https://www.linkedin.com/in/daniellemessler/ Natalie Taylor: https://www.linkedin.com/in/nataliecstaylor/ Capsule: https://capsule.video/ Planful: https://planful.com/ Mac Reddin: https://www.linkedin.com/in/mac-reddin/ David Politis: https://www.linkedin.com/in/davidpolitis/ Love the show? Give us a shoutout on LinkedIn and tell us what you loved!…
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The Transaction
1 Align and Conquer with Carlos Hidalgo - The Transaction - Ep # 30 49:36
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Play Later Play Later Lists Like LikedToday Matt and Craig open the floodgates to actionable marketing insights with seasoned guest, Carlos Hidalgo Co-Founder and CEO of Digital Exhaust. The episode focuses on the landscape of marketing, shedding light on the challenges and missteps related to AI, new technologies, and the tendency to chase after shiny objects. It examines the struggles CMOs face in balancing short-term demands with long-term strategies, emphasizing the significance of mutual respect and alignment between marketing, sales, finance, and product teams for sustainable success. Takeaways: Treat sales, finance, and product teams as partners. Spend dedicated time to understand their perspectives and needs, just as you would with external customers. Avoid reliance on broad ICP (Ideal Customer Profile) definitions. Instead, invest in detailed customer insights and keep them updated. Encourage shared goals amongst all business teams to foster a sense of joint accountability and drive consistent messaging and strategy. Resist the temptation to engage in short-term tactics at the expense of long-term strategy. Balance immediate actions with initiatives that build sustainable growth. Use customer insights to drive the creation of valuable content, campaigns, and product features that genuinely address customer pain points. Integrate sales feedback into marketing plans to ensure campaigns and content meet the practical needs of the sales process. Celebrate joint successes and publicly acknowledge contributions from different teams to reinforce the value of teamwork. Chapters: 00:00 Introduction / Why Are You Bitter Today? 02:08 Guest Introduction: Carlos Hidalgo 02:30 Carlos' Story: Meeting Craig 07:54 Market Misconceptions and Shiny Object Syndrome 08:57 The Importance of Customer Understanding 10:38 CMOs and the Seat at the Table 18:09 Alignment Across the Organization 25:58 Shared Goals and Compensation 27:47 Customer-Centric Marketing 28:18 Addressing Sales Roadblocks 32:41 The People Problem in Alignment 35:39 The Role of Marketing in Sales Success 38:10 Understanding the Customer 42:13 Final Thoughts and Conclusion Quote of the Show: “Growth doesn't go out of style. Growth has always been the goal.” - Carlos Hidalgo Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with Carlos: LinkedIn: https://www.linkedin.com/in/carlosahidalgo/ Website: https://digitalexhaust.co/ Shoutouts: Phil Fernandez https://www.linkedin.com/in/phil-fernandez-6902881/ Ray Rike https://www.linkedin.com/in/rayrike/ AJ Gandhi https://www.linkedin.com/in/anjaigandhi/ McAfee https://www.mcafee.com/ ZoomInfo https://www.zoominfo.com/ Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In: Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1…
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1 Building Trust and Reputation in Today's Market with Jon Miller - The Transaction - Ep # 029 48:54
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Play Later Play Later Lists Like LikedIn this episode, Matt and Craig welcome Jon Miller, Co-Founder of both Marketo and Engagio, who discusses the evolution of B2B marketing and sales strategies. They critique traditional methodologies like MQLs and programmatic email marketing, stressing the need for creativity and relationship-building. Key themes from this episode include the significance of content quality over quantity, customer-centric approaches, and the foundational role of market positioning and core fundamentals. The conversation explores the strategic shift required of modern CMOs, the importance of proprietary research, personal branding, and community building for reputation, and the necessity of evolving marketing metrics and reporting to reflect new market realities. Takeaways: Emphasize creating high-quality, valuable content that genuinely addresses the needs and interests of your target audience. Avoid the temptation to flood the market with low-value, high-volume content. Assess the effectiveness of current marketing tactics and adapt to evolving market dynamics. Consider moving away from outdated methods that no longer resonate with buyers. Shift the focus from treating buyers as leads to nurturing relationships and providing genuine value. Evaluate how your strategies impact customer satisfaction and loyalty. Use long-form content like podcasts, research reports, and comprehensive guides to build authority and engagement. Encourage key executives and thought leaders within the company to build their personal brands. This can amplify the company's reputation and provide a human touch to your corporate identity. Create content based on unique, proprietary data that your organization possesses. This positions your company as a thought leader and provides valuable insights that only you can offer. Invest in creating and nurturing vibrant communities both online and offline, including organizing events, fostering online forums, and creating spaces for meaningful interactions. Chapters: 00:00 - Discussing Matt’s Haircut 01:29 - Guest Introduction: Jon Miller 07:13 - Challenges in Modern Marketing 12:45 - Customer-Centric Strategies 20:48 - Content Creation and Market Education 24:35 - Reputation vs. Brand: Building Trust in the Marketplace 24:57 - Leveraging Personal Brands and Proprietary Research 29:06 - The Role of Community in Reputation Building 33:06 - Positioning and Differentiation: The Key to Market Success 40:53 - The Evolving Role of the CMO 43:48 - Concluding Thoughts Quote of the Show: “We've lost sight of the core fundamental. The true core fundamental is a mindset of what's right for the customer.” - Jon Miller Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with Jon: LinkedIn: https://www.linkedin.com/in/jonmiller2/ Website: https://www.jonmiller.com/ Shoutouts: Gretchen DeKnikker https://www.linkedin.com/in/gretchend/ Outreach https://www.outreach.io/ SalesLoft https://www.salesloft.com/ Gong https://www.gong.io/ Carta https://carta.com/ DemandBase https://www.demandbase.com/ Adam Robinson https://www.linkedin.com/in/retentionadam/ AudiencePlus https://audienceplus.com/ John-Henry Scherck https://www.linkedin.com/in/jhtscherck/ Rippling https://www.rippling.com/ AJ Gandhi https://www.linkedin.com/in/anjaigandhi/ Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In: Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1…
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1 Advisor Avengers: Assembling Your Network with Carilu Dietrich - The Transaction - Ep # 28 45:59
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Play Later Play Later Lists Like LikedIn this episode, Matt and Craig explore the role of advisors in driving B2B business growth with Carilu Dietrich, an ex-CMO and current hypergrowth advisor to CEOs and CMOs. Carilu shares her insights on the importance of having a skilled team of advisors to support executives, highlighting the need for different types of advisors at various growth stages. The discussion also delves into the nuances of building valuable professional networks and how to effectively seek and maintain advisory relationships. The episode emphasizes that the right advisory connections can be pivotal in determining the success and growth trajectory of a business. Takeaways: Determine the specific areas where your team lacks expertise and seek advisors who can fill those knowledge gaps. Create advisory roles with clear goals, timelines, and built-in review periods to ensure the relationship remains beneficial. Actively attend and engage in industry events and speaking engagements to build your network. Regularly nurture relationships with your network through periodic meetings and informal get-togethers to maintain strong connections. Maintain a small group of trusted individuals who are intimately familiar with your challenges and can provide immediate feedback. When reaching out to potential advisors or network connections, reference their work and specify how their expertise could help with your current challenges. Continuously assess the value derived from advisory relationships and refine your advisory strategy to better align with your evolving business needs. Chapters: 00:00 - Introducing B2B Famous 05:29 - The Importance of Advisors 10:10 - Building Trust with Advisors 14:08 - Effective Executive-Advisor Relationships 21:29 - The Value of Continuous Learning 23:37 - The Quest for Knowledge and Networking 25:06 - The Role of Advisors in Business 26:41 - Building and Leveraging Networks 30:43 - Effective Outreach Strategies 39:56 - The Importance of Layers in Networking 42:24 - Conclusion and Final Thoughts Quote of the Show: “Trust is the biggest currency we have in business.” - Carilu Dietrich Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with Carilu: LinkedIn: https://www.linkedin.com/in/cariludietrich/ Website: https://www.carilu.com/ Shoutouts: Maria Pergolino https://www.linkedin.com/in/mariapergolino/ Dennis Lyandres https://www.linkedin.com/in/dlyandres/ Atlassian https://www.atlassian.com/ 1Password https://1password.com/ Oracle https://www.oracle.com/ Rick Schultz https://www.linkedin.com/in/rischultz/ Databricks https://www.databricks.com/ Diego Lomanto https://www.linkedin.com/in/diegolomanto/ AJ Gandhi https://www.linkedin.com/in/anjaigandhi/ Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In: Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1…
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1 Triple T POV with Dan Gottlieb- The Transaction - Ep # 27 57:06
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Play Later Play Later Lists Like LikedIn this episode, Craig and Matt host Dan Gottlieb, Vice President Analyst at Gartner. They discuss sales strategies, highlighting the need for modern sales organizations to rethink their talent strategies, simplify sales processes, and intelligently apply technology. Dan shares insights from Gartner research on the competencies of high-performing sales reps and the importance of adaptability, tactical flexibility, and AI partnership. They also discuss the challenges and opportunities in adopting AI in sales, the value of point-of-view selling, and how technology can enhance sales tactics. Takeaways: Focus on hiring and developing talent that exhibits essential future skills like mentalizing, tactical flexibility, and AI partnership. Develop hiring processes that test these competencies through practical exercises and scenarios. Replace overly complex sales methodologies like MEDIC and MedPIC with simplified processes centered around developing a differentiated point of view and creating compelling business cases, making the sales process more agile and buyer-focused. Emphasize practical applications such as AI-led sales research and automated transcription summaries to optimize efficiency. Encourage sales teams to be creative and adaptable in their approach to customer interactions and deal-making. Move away from rigid sales processes that can stifle innovation and responsiveness. Implement visual and interactive tools, such as virtual whiteboards for discovery and technical discussions. These tools can enhance engagement and collaboration during the sales process. Simplify and streamline buyer interactions by maintaining a focus on value delivery at each stage of the sales process. Ensure that your sales methodologies take into account the total buyer journey from initial engagement to final sale. Shift focus from generic approaches to more tailored, client-specific solutions. This entails understanding client needs deeply and adjusting your offerings to meet those needs uniquely. Chapters: 00:00 - Discussing the Map and National Parks 02:34 - Introducing Dan Gottlieb 05:02 - Dan's Professional Journey 10:28 - Sales Strategies and Talent Acquisition 28:30 - Brief “Airplane” Reference 29:27 - Simplifying the Sales Process 31:15 - Exercises in Sales Interviews 32:50 - Point of View Selling 34:13 - Interactive Discovery Techniques 37:28 - AI in Sales Tech 42:24 - Challenges in AI Adoption 51:41 - Storytelling in Sales 56:05 - Closing out the Episode Quote of the Show: “Think about what great prospecting is. It's all about finding a point of view and delivering that in a time that makes sense with a message that makes sense, but it originates from a point of view.” - Dan Gottlieb Sponsor: The Transaction is sponsored by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with Dan: LinkedIn: https://www.linkedin.com/in/danielpgottlieb/ Website: https://www.gartner.com/en Shoutouts: Glacier National Park https://www.nps.gov/glac/index.htm Cutco https://www.cutco.com/ Miro https://miro.com/ Lucid Chart https://lucid.co/ ZoomInfo https://www.zoominfo.com/ Gong https://www.gong.io/ Outreach https://www.outreach.io/ Clari https://www.clari.com/ John Barrows https://www.linkedin.com/in/johnbarrows/ Ashley Welch https://www.linkedin.com/in/awelch1/ Microsoft CoPilot https://copilot.microsoft.com/ Jeremy Donovan https://www.linkedin.com/in/jeremeydonovan/ Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In: Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1…
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1 Navigating Market Success with AJ Gandhi - The Transaction - Ep # 26 53:52
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Play Later Play Later Lists Like LikedIn today’s episode, Matt and Craig are joined by AJ Gandhi, Chief Growth Officer at Marlin Equity. The discussion is an in-depth exploration of go-to-market (GTM) strategies. They cover the importance of core selling skills, the impact of over-reliant sales enablement tools, and the undervalued power of creative marketing. AJ emphasizes the critical role of coherent, cross-functional collaboration in GTM strategies and the need to reassess current methods to align with today's discerning buyers. They also discuss the importance of accurate marketing spend, talent development, and the overlooked strategic role of customer and partner funnels in driving business growth. Takeaways: Be realistic about growth objectives and ensure that spending on sales and marketing is justified by actual returns. Focus more on marketing activities influencing the self-managed buyer's journey as buyers become more self-sufficient. Prioritize marketing activities that can quantitatively demonstrate influence on the buyer’s journey rather than just focusing on attribution metrics. Define and rigorously pursue your Ideal Customer Profile (ICP). Create and maintain a targeted list of potential customers. Ensure all marketing and sales efforts are aligned with engaging this list. Implement structured hiring and talent assessment practices to ensure you are onboarding the right people. Ensure the CEO and executive team understand the value of different marketing and sales strategies and invest in the most promising approaches. Chapters: 00:00 - Introduction and Paella Party Realization 01:06 - AJ's Networking and Social Schedule 06:59 - The Value of In-Person Problem Solving 10:48 - Rethinking Go-To-Market Strategies 14:15 - The Importance of Marketing in the Buyer’s Journey 21:38 - Holistic Approach to Pipeline Management 28:50 - Marketing Spend and Attribution 41:24 - Challenges in Sales Talent Development 47:34 - Evaluating Marketing Investments 50:04 - Building a Winning Team 51:14 - Closing Thoughts and Farewell Quote of the Show: “People just need to step back and almost like forget all the stuff that they're doing that's part of the standard playbook. Take a step back and really think about what are we trying to do here and how do we actually influence these buyers’ dreams.” - AJ Gandhi Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with AJ: LinkedIn: https://www.linkedin.com/in/anjaigandhi/ Website: https://www.marlinequity.com/ Shoutouts: Sydney Sloan https://www.linkedin.com/in/sydsloan/ Ryan Azus https://www.linkedin.com/in/ryanazus/ RingCentral https://www.ringcentral.com/ Marc Benioff https://www.linkedin.com/in/marcbenioff/ Jen Igartua https://www.linkedin.com/in/jen-igartua/ Salesforce https://www.salesforce.com/ Guy Rubin https://www.linkedin.com/in/rubinguy/ Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In: Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1…
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1 From Siloed Heroics to Aligned Growth Playbooks with John Common - The Transaction - Ep # 25 57:35
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Play Later Play Later Lists Like LikedIn this episode of 'The Transaction,' Matt and Craig are joined by John Common, CEO of Intelligent Demand, to discuss various aspects of B2B growth strategy. The conversation focuses on the importance of different go-to-market motions, ICP targeting, and the implementation of cross-functional alignment. John stresses moving beyond tactical focus to strategic integration, operationalizing alignment, and realistically tackling people problems to achieve scalable growth. The episode wraps up with a focus on practical steps for CEOs and ELTs to improve business performance through clearly defined roles and metrics, and learning from successful case examples. Takeaways: Regularly assess and adjust the ICP (Ideal Customer Profile) to ensure that targeting remains focused and effective. This ensures marketing and sales aim at the most lucrative customer segments. Translate alignment from a conceptual level to actionable, everyday practices. Implement clear role definitions, SLAs, and regular cross-functional meetings to ensure sustained alignment. Distinguish between primary and secondary go-to-market motions. Focus resources on getting exceptionally good at one or two primary motions before expanding efforts. Constantly educate and train leadership and teams on effective go-to-market strategies and the importance of cross-functional collaboration. Consider establishing training programs or workshops for this purpose. Sales and marketing should collaborate closely during the budgeting process to ensure coherent and mutually supportive plans. Present a unified budget to the board to reinforce company-wide commitment to shared goals. When facing alignment or performance issues, carefully diagnose whether they stem from role misalignment, poor management, or cultural issues. Address these root causes rather than defaulting to replacing personnel The CEO or top leadership must set a strong precedent for cross-functional collaboration. Leaders should emphasize the importance of integrated strategies and reinforce them by example and mandate. Chapters: 00:00 - Craig’s Hat and John's Music 03:50 - Transition to Business Talk 05:19 - Discussing Business Alignment 08:28 - The Importance of Integrated Growth Plays 25:17 - Professed vs. Actual Alignment 29:05 - Realistic Expectations for Operators 29:26 - Challenges in Sales and Marketing Alignment 31:57 - Product Management in SMBs 33:21 - Scaling Post Product-Market Fit 36:49 - The Role of Heroics in Business Success 47:20 - Final Thoughts and Reflections Quote of the Show: “By doing more, you actually might be hurting your brand more, you might be pissing buyers off more, and you definitely will be wasting your budget more.” - John Common Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with John: LinkedIn: https://www.linkedin.com/in/johncommon/ Website: https://intelligentdemand.com/ Podcast: https://www.growthdrivershow.com/ Shoutouts: Mark Kosoglow https://www.linkedin.com/in/mkosoglow/ Ray Rike https://www.linkedin.com/in/rayrike/ Salesforce https://www.salesforce.com/ Definitive Guide to Lead Scoring https://business.adobe.com/resources/guides/lead-scoring.html Quartet https://www.quartet.com/ Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In: Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1…
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1 Pitching the Promised Land with Andy Raskin - The Transaction - Ep # 24 50:04
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Play Later Play Later Lists Like LikedToday Craig and Matt welcome guest Andy Raskin, a renowned figure in the B2B space. The discussion revolves around the importance of creating impactful sales narratives. They discuss the structure and strategy behind compelling sales decks, leaning on examples like the famous Zuora deck. Andy shares insights on transitioning from founder-led sales pitches to scalable narratives and emphasizes the significance of CEO involvement in crafting these stories. The conversation also explores how narratives can frame market changes and embody a movement, making them more relatable and engaging for diverse audiences. Takeaways: Emphasize understanding and communicating the significant shifts in the market. Define the transition from the old way of doing things to the new, improved method. This helps in making the change more tangible and understandable for the audience. Clearly describe the benefits or the "promised land" that will be achieved by adopting the new approach or mindset. Ensure that the CEO or top leadership is deeply involved in crafting and telling the company’s story. This helps align the entire organization around a unified narrative. Include insights from sales, marketing, product, and other relevant teams to enrich the narrative with diverse perspectives and validate its applicability across different functions. Utilize the same narrative across various contexts like sales meetings, investor presentations, media interactions, and recruiting conversations to maintain consistency and reinforce the message. Revisit and adjust the narrative as the company grows, especially when integrating new acquisitions or entering new markets. Ensure the core story remains relevant and compelling as the business landscape evolves. Chapters: 00:00 - Welcome to Foster City 01:13 - Introducing Andy Raskin 02:02 - The Greatest Sales Deck Ever 04:43 - The Power of Movements in Business 17:59 - The Subscription Economy 23:07 - The Importance of CEO Involvement in Sales Decks 26:16 - Challenges in Replicating Founder's Passion 27:21 - Crafting a Compelling Narrative 27:59 - The Role of the CEO in Shaping the Narrative 29:27 - Key Points in a Company's Growth 31:29 - Teasing the Promised Land 36:00 - Identifying and Overcoming Obstacles 43:51 - The Power of a Unique Story 48:02 - Final Thoughts and Closing Remarks Quote of the Show: “He’s championing a movement, and I think the best leaders, I'm not even talking about marketers, I'm talking about CEOs, frame their companies this way.” - Andy Raskin Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with Andy: LinkedIn: https://www.linkedin.com/in/andyraskin/ Website: https://andyraskin.com/ Shoutouts: Zuora https://www.zuora.com/ Marc Benioff https://www.linkedin.com/in/marcbenioff/ Barnes and Noble https://www.barnesandnoble.com/ Salesforce https://www.salesforce.com/ Tien Tzuo https://www.linkedin.com/in/tientzuo/ Dreamforce https://www.salesforce.com/dreamforce/ One Trust https://www.onetrust.com/ Chris Voss https://www.linkedin.com/in/christophervoss/ Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In: Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1…
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1 Becoming a LinkedIn Master with Alec Paul - The Transaction - Ep # 23 56:07
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Play Later Play Later Lists Like LikedIn this episode, Matt and Craig delve into the evolving landscape of LinkedIn as a key platform for B2B thought leadership and brand building with the insights of Alec Paul, a LinkedIn strategist and Founder of SalesBrand. Alec discusses the significance of authenticity, audience engagement, and the potential of LinkedIn video. The conversation also covers the limitations and strategies for optimizing LinkedIn profiles, promoting podcasts, and understanding LinkedIn's algorithm. This episode is a deep dive into actionable strategies that can transform LinkedIn into a powerful tool for business growth. Takeaways: Encourage executives and key leaders to build their personal brands on LinkedIn. This creates authenticity and can serve as a powerful channel for engagement and outreach. Share personal experiences, including successes and failures, to build trust and depth with your audience. Vulnerability makes leaders relatable and credible. Focus on producing high-quality, engaging content rather than flooding your feed with frequent, less impactful posts. Two to three well-crafted posts can be more effective than daily low-value content. While having a content calendar is useful, remain flexible to adjust based on what is resonating with the audience. Be prepared to pivot based on feedback and engagement metrics. Use podcasts or episodic videos to create compelling LinkedIn posts. Focus on extracting interesting stories or key insights from these content forms to create high-engagement posts. Ensure that LinkedIn profiles are well-crafted with a clear narrative. Include a professional banner image, a strong headline, and a detailed resume that aligns with the content being posted. Weave the company’s story into personal content authentically. Share insights into company decisions, product launches, and behind-the-scenes activities to engage the audience deeply. Chapters: 00:00 - Gen Z Slang 03:42 - Guest Introduction: Alec Paul 06:05 - The Importance of Personal Branding on LinkedIn 07:58 - Common Misconceptions About Outsourcing Content 11:07 - Getting Started with LinkedIn Content 17:39 - Finding Content Market Fit 25:30 - The Sixth Sense Approach in Startups 27:45 - Building Credibility Through Transparency 30:20 - Turning Companies into Characters 33:35 - The Role of Executives in Social Media 38:54 - Leveraging Executive Brands for Go-to-Market 47:19 - Challenges and Strategies in Podcast Promotion 49:40 - (Not) Understanding LinkedIn's Algorithm 54:07 - Concluding Thoughts and Future Insights Quote of the Show: “You want to learn the best practices and different forms of engagement or writing, but you still need to be the most authentic you.” - Alec Paul Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with Alec: LinkedIn: https://www.linkedin.com/in/alecjpaul/ Shoutouts: Adam Robinson https://www.linkedin.com/in/retentionadam Sam Jacobs https://www.linkedin.com/in/samfjacobs Pavilion https://www.joinpavilion.com/ Snowflake https://www.snowflake.com/en/ Sridhar Ramaswamy https://www.linkedin.com/in/sridhar-ramaswamy John Miller https://www.linkedin.com/in/jonmiller2 Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In: Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1…
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1 Which Metrics ACTUALLY Matter for B2B Marketers with Ray Rike - Ep 22 56:00
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Play Later Play Later Lists Like LikedIn this episode of The Transaction, Hosts Matt Amundson and Craig Rosenberg are joined by Ray Rike, the Founder and CEO of BenchmarkIt and the Co-Host of SaaS Talk, to delve into the world of metrics. Ray shares his passion for allowing SaaS operators to make metric-informed and benchmark-validated decisions by looking at metrics across the entire customer journey. He highlights key metrics such as CAC ratio, inbound hand raisers, and expansion CAC ratio, emphasizing their crucial roles in making informed business decisions. The conversation also explores the significance of shared goals among go-to-market teams and the need for a detailed analysis of the sales funnel. The episode wraps up with actionable insights on optimizing sales and marketing investments to improve efficiency and drive sustainable growth. Takeaways: Move beyond just tracking the number of top-of-funnel leads. Look at long-term metrics such as the percentage of qualified pipeline from inbound hand raisers and the efficiency metrics like CAC ratio. Ensure that both the CMO and the CRO have shared goals that include both pipeline and revenue numbers. This shared accountability can drive better collaboration and overall performance. Track metrics such as cycle time, average contract value (ACV), and win rates for inbound hand raisers compared to outbound sourced leads to better understand the efficiency of your marketing efforts. Break down pipeline sources by marketing, outbound sales development, direct sales, and channel partners. Assess pipeline coverage ratios and CAC ratios for each source to identify inefficiencies. Adopt rolling metrics, such as five or nine months, to track the long-term impact of marketing investments like podcasts or large content initiatives. Set AE-specific pipeline goals and offer incentives for AE-generated opportunities to improve the balance and efficiency of pipeline creation. As your company scales, regularly reassess and reallocate resources between new customer acquisition and existing customer expansion to optimize efficiency and growth. Chapters: 00:00 - Matt's Tardiness & Ray's GE Story 01:40 - Introduction to Ray Rike, the Founder & CEO of Benchmarkit 03:37 - Ray's Mission: Understanding SaaS Metrics & Benchmarks 08:11 - B2B Marketing Metrics: CAC Ratio and Pipeline Efficiency 11:43 - Deep Dive: CAC Ratio and Marketing Spend for SaaS Startups 25:26 - Sales Development & Pipeline Coverage in B2B 29:27 - Pipeline Challenges & Inefficiencies in B2B SaaS 32:49 - The Importance of Go-to-Market Alignment for Startups 34:16 - Evaluating SDR Performance and Metrics for Sales Leaders 35:41 - Optimizing Startup Growth in a Capital-Constrained Environment 41:15 - Shared Goals and Collaboration in B2B Sales & Marketing teams 49:33 - The Impact of Expansion CAC Ratio 53:59 - Concluding Thoughts and Key Takeaways Quote of the Show: “I believe that shared goals that are measurable by metrics help with alignment and integration of a go-to-market team.” - Ray Rike Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with Guest: Guest LinkedIn: https://www.linkedin.com/in/rayrike/ Guest Website: https://www.benchmarkit.ai/ Shoutouts: Dave Kellogg https://www.linkedin.com/in/kelloggdave/ SaaS Talk with the Metrics Brothers https://www.benchmarkit.ai/saas-talk SaaS Metrics Palooza https://www.benchmarkit.ai/saas-metrics-palooza Byron Dieter https://www.linkedin.com/in/byrondeeter/ Bessemer https://www.bvp.com/ Dave Spitz https://www.linkedin.com/in/dspitz/ Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In: Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1…
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The Transaction
1 The New Playbook: Signal Based Selling with Jen Igartua - The Transaction - Ep # 21 48:28
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Play Later Play Later Lists Like LikedThe Transaction’s guest today is one of many talents. Jen Igartua, who is not only the CEO of GoNimbly but also a side hustler in both comedy and board game designing, provides her insights on the sales and marketing world today. The conversation covers transforming B2B sales strategies using signal-based selling and PLG (Product-Led Growth) insights. Jen shares her innovative approach of using algorithmic scoring and playbooks to refine lead scoring and offering specific actionable insights for sales teams. She emphasizes the importance of integrating data from diverse sources and creating systems in Salesforce to optimize outcomes. The discussion also touches on evolving roles for SDRs and leveraging automation to enhance their effectiveness. Towards the end, Jen shares her side venture as a board game designer and the unexpected success of her game, 'Side Effects.' Takeaways: Develop a system that triggers alerts and notifications based on specific business signals, ensuring those signals are integrated into CRM platforms like Salesforce for easy access by sales teams. Deliver summarized and relevant data insights to the sales team. Ensure that raw data is processed into actionable information, with clear next steps included. Design playbooks that align with specific triggers and signals, providing the sales team with structured guidance on how to respond and engage clients based on the data insights. Ensure that all customer interactions, whether in marketing or sales, are unified in a single repository like a data warehouse and accessible from the CRM. This avoids silos and allows for a holistic view of client engagement. Consider automating the initial touchpoints of outbound campaigns through marketing, and then routing the responses and qualified leads to SDRs for further personalized engagement. Move beyond traditional lead scoring to a more outcome-focused model that considers multiple signals for different stages of the customer lifecycle, such as expansion opportunities and churn risks. Even with automation, ensure that meaningful human interactions remain a core part of the sales process, particularly for high-value touchpoints. Chapters: 00:00 - Jen's Comedy Career 01:28 - Welcoming Jen Igartua 02:48 - Jen's Background and Experience 03:28 - The Big Question 04:12 - Shifts in Lead Scoring 07:10 - Intercom's Tactical Example 08:40 - Challenges in Signal-Based Selling 14:29 - Building Effective Sales Playbooks 18:39 - Integrating Signals into Salesforce 25:10 - Leveraging High Usage Data for AI Product Pitches 26:01 - Effective Playbooks and Workflow Integration 27:05 - The Shift to Data Warehouses 29:29 - The Role and Future of SDRs in Sales 33:27 - The Human Element in Sales Automation 42:44 - Exploring the Side Hustle: Board Game Design 46:53 - Conclusion and Final Thoughts Quote of the Show: “It’s rare that you actually see folks really putting themselves in the customer’s shoes and saying ‘What do they actually need?’” - Jen Igartua Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with Jen: Jen’s LinkedIn: https://www.linkedin.com/in/jen-igartua/ Website: https://gonimbly.com/ Shoutouts: Scott Brinker https://www.linkedin.com/in/sjbrinker/ Esteban Kolsky https://www.linkedin.com/in/estebankolsky/ EverString https://lsvp.com/company/everstring/ Salesforce https://www.salesforce.com/ Intercom https://www.intercom.com/ Twilio https://www.twilio.com/en-us Ashley Welch https://www.linkedin.com/in/awelch1/ Dave Brock https://www.linkedin.com/in/davebrock/ Zendesk https://www.zendesk.com/ Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In: Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1…
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The Transaction
1 Unlocking Sales Success: Creativity Over Volume with Mark Kosoglow - The Transaction - Ep # 20 52:56
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Play Later Play Later Lists Like LikedToday Mark Kosoglow, an experienced sales professional and an advisor at HockeyStack, discusses with Craig and Matt his insightful perspectives on sales strategies. He emphasizes the importance of creativity over sheer volume in outreach and the challenges posed by current sales practices. Mark highlights his approach to sales from his time at Outreach, underscoring the significance of business acumen, the use of relevant buyer experiences, and the concept of a 'buyer room.' The discussion also explores the effectiveness and potential drawbacks of digital sales rooms and inbound-led outbound strategies, concluding with a reflection on the importance of helping buyers make confident decisions. Takeaways: Evaluate and shift from increasing touchpoints to enhancing the quality of interactions. Encourage your sales team to prioritize meaningful, well-crafted communications rather than mass outreaches. Train your sales team to understand and analyze business data, industry trends, and customer insights. Develop sales processes and tools that are centered on the buyer’s journey. Consider introducing tools or methodologies that allow for co-creation with buyers to make them feel more involved and valued in the sales process. Leverage platforms like Slack where your customers are already active. Integrate your sales communications and materials into these existing workflows to increase adoption and engagement. Foster an environment where creativity is valued and different approaches are encouraged. This can help your team stand out in a crowded market. Reduce friction points for potential customers, like unnecessary qualification steps. Make it easier for them to get the information and demos they need, minimizing any barriers to engagement. Use AI to enhance the buyer’s experience, such as providing insights and recommendations based on their interactions. However, be wary of over-automation that could lead to impersonal experiences. Chapters: 00:00 - Introduction and Story Swapping 02:46 - Endorsements and Praise for Mark 04:25 - Sales Leadership and Challenges 06:44 - The Problem with Sales Touches 14:04 - Creativity in Sales 16:45 - Business Acumen in Sales 22:11 - Marketing and Personalization 24:31 - Sales Rooms Discussion 27:10 - The Buyer's Perspective on Digital Sales Rooms 28:46 - Real-World Sales Cycle Example 30:26 - The Concept of a Buyer Room 39:26 - Inbound vs. Outbound Marketing Debate 44:22 - Reimagining the Sales Demo Process 51:29 - Final Thoughts and Conclusion Quote of the Show: “Sales is a numbers game, but unfortunately there's two sides to that coin. One is if you don't do enough, you won't get results. The other one is if you do too much, you won't get results.” - Mark Kosoglow Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with Guest: Mark’s LinkedIn: https://www.linkedin.com/in/mkosoglow/ Shoutouts: Doug Landis https://www.linkedin.com/in/douglandis/ Outreach https://www.outreach.io/ Adam Robinson https://www.linkedin.com/in/retentionadam/ Little Red Book of Selling https://www.amazon.com/Little-Red-Book-Selling-Principles/dp/1885167601 Catalyst https://catalyst.io/ Dave Brock https://www.linkedin.com/in/davebrock/ Slack https://slack.com/ Matt Dixon https://www.linkedin.com/in/matthewxdixon/ Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/…
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1 People Strategy: Hiring, Firing, and Leadership with Dennis Lyandres - The Transaction - Ep # 19 53:00
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Play Later Play Later Lists Like LikedThis episode brings on Dennis Lyandres as the guest. He is currently an advisor at ICONIQ Capital and has many years of sales, marketing, and strategy experience. Along with Craig and Matt, Dennis discusses effective leadership techniques and the importance of relentless learning in the sales and marketing world. He emphasizes the importance of hiring curious, humble, and growth-oriented individuals. The conversation covers critical aspects of scaling a business, such as proactive hiring and firing practices, leadership development, and leveraging unique people strategies. They stress the need for purposeful learning and personalized development plans to foster great leaders and retain high-performing teams. This episode is chalked full of insight from Dennis, listen to hear more! Takeaways: When hiring, focus on vetting candidates for qualities such as curiosity, humility, and a growth mindset. These attributes can significantly impact their success and the culture of the organization. Effective firing is crucial. While hiring is about adding value, firing ensures that non-performing or culture-misaligned individuals do not hinder organizational progress. Handle firings with dignity and as potential growth opportunities for those individuals. Encourage a culture of continuous learning and development. This contributes to better leadership and organizational adaptability. Building and maintaining trust within the team is essential. Transparency in operations, especially involving key metrics and strategic goals, can significantly enhance trust and performance. Ensure that sales leaders and managers are adept at the core competencies and are continuously certified in areas like product knowledge and pitching. The B2B sales and marketing world evolves rapidly. Leaders need to stay updated and adapt quickly to avoid obsolescence. Chapters: 00:00 Dennis's Story: From Cloudera to Procore 02:34 Welcoming Dennis Lyandres 03:16 The Rapid Evolution of B2B Sales and Marketing 05:59 The Importance of People Strategy in Business 10:20 Hiring and Firing: Key Leadership Insights 16:09 Curiosity and Learning in Sales 19:23 The Role of Leadership in Organizational Success 27:33 The Excitement of Hiring vs. The Dread of Firing 29:30 The Importance of Effective Firing 32:01 Learning and Development in Leadership 36:30 Transparency and Leadership Development 40:53 Tailoring Enablement Programs for Leaders 47:44 Developing Marketing Leaders 51:19 Conclusion and Final Thoughts Quote of the Show: “I'm willing to bet that leadership is the most important thing to winning, that training and development are super important.” - Dennis Lyandres Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with Dennis: Dennis’ LinkedIn: https://www.linkedin.com/in/dlyandres/ Website: https://www.iconiqcapital.com/ Shoutouts: Cloudera https://www.cloudera.com/ Lars Nilsson https://www.linkedin.com/in/lanilsson/ Procore https://www.procore.com/ SalesLoft https://www.salesloft.com/ Robert Koehler https://www.linkedin.com/in/rkoehler/ Carol Dweck https://profiles.stanford.edu/carol-dweck Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/…
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The Transaction
1 Unlocking Strategic Marketing with Sydney Sloan - The Transaction - Ep # 18 46:41
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Play Later Play Later Lists Like LikedToday’s episode welcomes Sydney Sloan, former CMO of Drata and newest CMO of G2, to sit down with Craig and Matt to give strong insights on the evolving strategies being used in marketing. Sydney discusses the shift from account-based to segment-based strategies, and elaborates on how triangulation of data points can enhance targeting and campaign effectiveness. The discussion also covers practical approaches centered on data-backed decision-making, the importance of regular updates, and optimizing digital channels. Sydney emphasizes the necessity of clean data, strong branding, and a focused organic LinkedIn strategy. Listen now to hear her personal insights and hear examples from her experience! Takeaways: Marketers should consider evolving traditional account-based marketing (ABM) strategies to focus more on segment-based strategies. This involves identifying segments based on a combination of data points (like industry, buyer type, and pain points) rather than individual accounts. Keep your campaigns simple and focused. Instead of spreading your efforts too thin across multiple channels or segments, concentrate on a few high-impact segments and execute them well. Utilize both qualitative and quantitative data to inform decisions on where to invest marketing and sales efforts. This includes building financial models to forecast potential ARR from various segments. Leverage partnerships with platforms like Google and LinkedIn. Actively engage with platform representatives to get the most out of your ad spend and learn best practices. Focus on a few key industry events and participate in a big way to make a memorable impact. It’s better to show up strong at a few events than to have a diluted presence across many. Integrate both organic and paid strategies on platforms like LinkedIn. Use employees and satisfied customers to generate organic content that complements paid efforts. Ensure your brand voice is consistent across all channels, especially when spending on paid advertisements. Brand alignment is crucial for effective demand capture. Chapters: 00:00 - Icebreaker: Dream Jobs 1:49 - Intro: Sydney Sloan 4:27 - Goodbye Account-Based Approaches 9:44 - Creating Effective Segments 18:50 - Implementing Segment Strategies 24:10 - Building a Simple Segment Strategy 25:49 - Channel Strategies: What Works and What Doesn’t 28:54 - Going Big at Events: Strategic Success 35:38 - Importance of Organic LinkedIn 45:10 - Closing Thoughts/Outro Quote of the Show: “The choice that I made was we're not going to go to every show, but the shows we do go to, we're going to go big.” - Sydney Sloan Sponsor: The Transaction is sponsored and produced by Ringmaster, on a mission to create connections through Branded podcasts . Learn more at https://ringmaster.com/ Connect with Guest: Sydney’s LinkedIn: https://www.linkedin.com/in/sydsloan/ Shoutouts: Drata https://drata.com/ Salesloft https://www.salesloft.com/ KnowBe4 https://www.knowbe4.com/ Nicolas de Kouchkovsky https://www.linkedin.com/in/nicolask3/ Lisa Horner https://www.linkedin.com/in/lisahorner/ Okta https://www.okta.com/ Sprout Social https://sproutsocial.com/ Follow the Show: Craig’s LinkedIn: https://www.linkedin.com/in/craigrosenberg/ Matt’s LinkedIn: https://www.linkedin.com/in/matt-amundson-91657236/ The Transaction on LinkedIn: https://www.linkedin.com/company/the-transaction/ The Transaction Website: https://thetransactionpod.com/ Substack: https://thetransaction.substack.com/ Ways to Tune In: Spotify: https://open.spotify.com/show/3i3r3WLacRZiSa7dOaOgDz Apple Podcasts: https://podcasts.apple.com/us/podcast/the-transaction/id1734518309 YouTube: https://www.youtube.com/@TheTransaction?sub_confirmation=1…
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