GTM 142: Why Most B2B Marketing Fails (And How to Fix It) with Udi Ledergor

The GTM Podcast

13:44

Legendary actor and mental health advocate Glenn Close is on a quest to change how we think about mental health, starting with her decision to speak out about her own family's struggles — a brave choice considering the stigma that pervades the topic. This week, we're revisiting this sweeping conversation with TEDWomen curator Pat Mitchell, where Close shares the inspiration behind the advocacy group she founded to combat the crisis, underscoring the transformative power of community and the critical need for comprehensive mental health care systems. Want to help shape TED’s shows going forward? Fill out our survey ! Become a TED Member today at https://ted.com/join Hosted on Acast. See acast.com/privacy for more information.…

about a year ago 56:47

MP3•Episode home

Discussed in this Episode:

Why Marketing 'Best Practices' are broken for Brands that want to stand out.
Marketers need to consider the long game and remember the 95/5 rule.
When you should hire for experience versus potential.
How to foster a culture of healthy risk-taking with your team.

Highlights:

04:09 Udi's inspiration for writing his new book, Courageous Marketing.

06:02 The four most common reasons why marketing fails.

09:22 What marketers should be looking for when selecting a company to join.

13:55 The Problem with 'playing it safe' in B2B marketing.

23:07 How to market to both the 5% and the 95% of your buyers.

38:13 The Three Team Operating Principles for leading a bold and effective marketing team.

Guest Speaker Links (Udi Ledergor):

LinkedIn: https://www.linkedin.com/in/udiledergor/
Gong: https://www.gong.io/
Udi's Book, Courageous Marketing: https://mybook.to/courageousmarketing

Host Speaker Links (Sophie Buonassisi):

LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
Newsletter: https://gtmnow.com/tag/newsletter/

Where to find GTMnow (GTMfund’s media brand):

Website: https://gtmnow.com/
LinkedIn: https://www.linkedin.com/company/gtmnow/
Twitter/X: https://x.com/GTMnow_
YouTube: / @gtm_now
The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/

Sponsor: ZoomInfo’s GTM25 Virtual Conference—a free, half-day event on h

The GTM Podcast
The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.
Visit gtmnow.com for more episodes and other interesting content.

Chapters

1. GTM 142 - Udi Ledergor - Full Episode 1.1 (00:00:00)

2. Udi's inspiration for writing his new book, Courageous Marketing (00:03:08)

3. The four most common reasons that marketing fails (00:05:50)

714 episodes

GTM 142: Why Most B2B Marketing Fails (And How to Fix It) with Udi Ledergor

The GTM Podcast

100 subscribers

published about a year ago

MP3•Episode home

Discussed in this Episode:

Why Marketing 'Best Practices' are broken for Brands that want to stand out.
Marketers need to consider the long game and remember the 95/5 rule.
When you should hire for experience versus potential.
How to foster a culture of healthy risk-taking with your team.

Highlights:

04:09 Udi's inspiration for writing his new book, Courageous Marketing.

06:02 The four most common reasons why marketing fails.

09:22 What marketers should be looking for when selecting a company to join.

13:55 The Problem with 'playing it safe' in B2B marketing.

23:07 How to market to both the 5% and the 95% of your buyers.

38:13 The Three Team Operating Principles for leading a bold and effective marketing team.

Guest Speaker Links (Udi Ledergor):

LinkedIn: https://www.linkedin.com/in/udiledergor/
Gong: https://www.gong.io/
Udi's Book, Courageous Marketing: https://mybook.to/courageousmarketing

Host Speaker Links (Sophie Buonassisi):

LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/
Newsletter: https://gtmnow.com/tag/newsletter/

Where to find GTMnow (GTMfund’s media brand):

Website: https://gtmnow.com/
LinkedIn: https://www.linkedin.com/company/gtmnow/
Twitter/X: https://x.com/GTMnow_
YouTube: / @gtm_now
The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/

Sponsor: ZoomInfo’s GTM25 Virtual Conference—a free, half-day event on h

Chapters

1. GTM 142 - Udi Ledergor - Full Episode 1.1 (00:00:00)

2. Udi's inspiration for writing his new book, Courageous Marketing (00:03:08)

3. The four most common reasons that marketing fails (00:05:50)

714 episodes

All episodes

The GTM Podcast

1
GTM 150: 80% of Exec Roles Aren’t Posted, Here's How to Land Them Anyway with Andy Mowat 48:22

3 days ago48:22

48:22

Andy Mowat is the Co-Founder of Whispered, and is responsible for building incredible RevOps and GTM systems at unicorns like Upwork, Box, and Culture Amp. With over two decades of experience leading marketing ops, sales ops, and go-to-market infrastructure, Andy is a true pioneer of modern RevOps. Today, he’s building tools to help tech executives collaborate on company insights, search strategies, introductions, and the deepest database of unposted GTM roles anywhere. Discussed in this Episode: - Why 80–98% of VP and C-level roles are never posted—and how to access them. - The importance of clarity: how GTM operators should articulate their focus to stand out. - How venture networks and backchanneling drive most executive hiring decisions. - The rise (and limits) of fractional work as a bridge between full-time roles. - What AI agents are doing behind the scenes at Whispered to match execs to roles. - Why company stage, growth rate, and CEO quality are critical in picking your next role. - What GTM functions (e.g. RevOps, Demand Gen) are most in-demand right now. Highlights: 04:30 Why most executive roles are never posted 07:00 How Whispered operates as a curated talent network 13:30 Why GTM execs struggle to articulate their focus—and how to fix it 16:45 The right way to build a target company list 21:00 Engaging your network and VC talent teams the right way 28:00 What AI is (and isn’t) changing about hiring and team structure 34:00 How to evaluate growth-stage companies and pick winners 36:30 Head of vs. VP vs. CRO: The real meaning of title across company sizes 41:00 Most common mistakes execs make in their job search 44:30 Using customer advocacy and growth loops to scale Whispered 46:00 Is email dead? Why it's still critical to GTM and talent outreach Guest Speaker Links (Andy Mowat): - LinkedIn: https://www.linkedin.com/in/amowat/ - Whispered: https://www.whispered.com/ Host Speaker Links (Sophie Buonassisi): - LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ - Newsletter: https://substack.com/@sophiebuonassisi Where to find GTMnow (GTMfund’s media brand): - Website: https://gtmnow.com/ - LinkedIn: https://www.linkedin.com/company/gtmnow/ - Twitter/X: https://x.com/GTMnow_ - YouTube: @gtm_now - The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/ Sponsor: Qualified Qualified is the Agentic Marketing Platform with the world's leading SDR agent, Piper the AI SDR. Marketing teams trust Piper to autonomously drive inbound pipeline at scale, delivering real-time engagement and conversion. Trusted by top brands like Asana, Box, Brex, Clari, GE Healthcare, and more, Qualified is redefining how companies generate pipeline in the age of AI. Sponsor Link: https://www.qualified.com/plus/category/ai-sdr-summit?utm_source=gtmfund The GTM Podcast Don’t miss The GTM Podcast dropping every Tuesday discussing true stories and experiences including trials and tribulations in the Go-To-Market world. #career #jobsearch #techcareers The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

1
GTM 149: How to Scale International Sales Teams with Rick Kelley 46:56

10 days ago46:56

46:56

Rick Kelley is the former SVP of Gaming & App Monetization Solutions at Meta and Managing Director of Meta Ireland, where he led a $1B+ revenue organization & played a pivotal role in building out Meta’s go-to-market teams across North America & EMEA. Over his 15-year career at Meta, Rick was instrumental in driving international expansion, especially across Europe, the Middle East, & Africa—helping to localize strategy, scale high-performing sales teams, & bring new ad products to market. Today, he advises founders on global GTM execution, sales hiring, & how AI is reshaping the future of commercial organizations. Discussed in this Episode: The operational playbooks that scaled Meta’s ad sales Why AI will shift how sales orgs think about headcount & human capital The three traits Rick looks for in great sales leaders—& how to spot them early Why early-stage companies should prioritize hiring builders, not closers How to segment go-to-market motions by customer journey, not just ACV Why “coachable, humble, gritty” still wins—even in an AI-powered GTM world Highlights: 6:30 How Meta scaled repeatable playbooks across SMB, Mid-Market, & Enterprise 10:00 The role of humility & coachability in building scalable teams 13:00 Why top sales leaders are systems thinkers—not just great closers 16:00 AI’s impact on headcount & how to scale without over-hiring 21:00 Making your first 5 sales hires count 25:30 Early-stage mistake: over-complicating GTM before validating demand 30:30 Why product & GTM must be tied at the hip—especially in AI-first companies 34:00 From Facebook to Meta: what changed & what didn’t in sales strategy 37:00 Final thoughts: GTM myths, leadership advice, & staying grounded Guest Speaker Links (Rick Kelley): LinkedIn: linkedin.com/in/rickkelley Host Speaker Links (Sophie Buonassisi): LinkedIn: linkedin.com/in/sophiebuonassisi Newsletter: substack.com/@sophiebuonassisi Where to find GTMnow (GTMfund’s media brand): Website: gtmnow.com LinkedIn: linkedin.com/company/gtmnow Twitter/X: x.com/GTMnow_ YouTube: /@gtm_now Sponsors: UserEvidence UserEvidence is the Cust The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

1
GTM 148: Winning Every Tech Shift from a 3X Founder (From Internet to AI) 54:31

17 days ago54:31

54:31

Sean Whiteley is a three-time founder and the Co-Founder of Qualified, the AI pipeline automation platform purpose-built for inbound GTM teams. Previously, he founded GetFeedback (acquired by Campaign Monitor) and Kieden (acquired by Salesforce), where he also served as SVP & GM. With over two decades at the forefront of tech’s biggest transformations—from on-prem to cloud to AI—Sean offers a rare, long-term view on how to build companies and go-to-market engines in the face of massive disruption. Discussed in this Episode: Why the speed of AI adoption outpaces every previous tech wave How the role of RevOps and team design is being reshaped by agentic systems Why today’s buyer journey is nonlinear, AI-assisted, and fully in control Tactical breakdown: how Sean mapped and tagged every task at Qualified for AI automation Why success teams must sit at the core of GTM strategy, not as an afterthought The most common GTM myth Sean is seeing today—and why it’s outdated The characteristics Sean looks for in long-term co-founders and GTM hires Highlights: 02:00 Sean’s journey through on-prem, cloud, and now AI 05:00 Ops leaders as the new AI orchestrators inside GTM teams 08:30 From workflows to autonomous agents: how org charts are shifting 10:30 The “two-way doors” mindset for fast experimentation 13:30 The future of GTM: agents, trust falls, and buyer-led journeys 15:00 From personalization to “relevance at scale” in modern marketing 18:00 AI unlocks speed and efficiency—how that reshapes CAC payback and TCO 24:00 How Qualified created internal AI blueprints across every team 28:30 Inside the AI SDR: replacing manual inbound sales with 24/7 automation 32:00 Success is not post-sales—it’s the center of the GTM experience 36:00 Reinventing yourself as a founder through three companies 39:30 What still hasn’t changed: customer value and trusted partnerships 47:00 GTM myth: “We control the buying process”—why that’s dead 51:00 Where Sean learns about AI: customer conversations > thought leadership Guest Speaker Links (Sean Whitely): LinkedIn: https://www.linkedin.com/in/seanwhiteley Qualified Website: https://www.qualified.com Host Speaker Links (Sophie Buonassisi): LinkedIn: https://www.linkedin.com/in/sophiebuonassisi Newsletter: https://substack.com/@sophiebuonassisi Where to find GTMnow (GTMfund’s media brand): Website: https://gtmnow.com LinkedIn: https://www.linkedin.com/company/gtmnow Twitter/X: https://x.com/GTMnow_ YouTube: @gtm_now The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/ The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

1
GTM 147: RevOps Is a Hidden Growth Engine with Navin Persaud, VP of RevOps at 1Password 42:16

24 days ago42:16

42:16

Navin Persaud is the VP of Revenue Operations at 1Password, where he leads a 30+ person team supporting a GTM org of 450+. With over 20 years of experience across RevOps, SalesOps, and MarketingOps, including time at IBM and high-growth SaaS companies, Navin has built a reputation as one of the sharpest operators in the game. He’s known for building scalable systems, ruthless prioritization, and a clear-eyed view of how AI is reshaping operations. Discussed in this Episode: Why RevOps is the most essential team for scalable growth The real signs that it’s time to hire your first RevOps leader What AI is disrupting first in RevOps forecasting, enrichment, orchestration, and reporting The rise of GTM Engineers and the shift toward intelligence-layer operations Tactical frameworks for combining AI insights with human judgment How RevOps should evolve from executor to strategic growth partner Hiring advice: what makes a great early-stage ops hire and how to test for curiosity Highlights: 05:00 - The sports field analogy: building the GTM pitch, not just playing on it 07:00 - AI is both the scariest and most freeing technology in ops today 09:00 - GTM Engineers and the orchestration opportunity ahead 11:00 - Product-market fit is the right time to invest in RevOps 13:00 Forecasting, enrichment, and demand routing—where AI adds leverage 17:30 -Why dashboards are dying and how ops will move to real-time insights 27:00 - How RevOps became a central GTM function 30:00 - Advice for founders on when (and how) to bring in ops leadership 33:00 - “Perfection is the enemy of pace”—a RevOps mantra Guest Speaker Links (Navin Persaud): LinkedIn: https://www.linkedin.com/in/navinpersaud/ 1Password: https://1password.com/ 1Password Careers: https://1password.com/careers Host Speaker Links (Sophie Buonassisi): LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ Newsletter: https://substack.com/@sophiebuonassisi Where to find GTMnow (GTMfund’s media brand): Website: https://gtmnow.com/ LinkedIn: https://www.linkedin.com/company/gtmnow/ Twitter/X: https://x.com/GTMnow_ YouTube: @gtm_now The GTM Podcast (on all major directories): The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

1
GTM 146: The Future of Search, AI, and Digital Presence with Mike Walrath, CEO of Yext 38:43

4 weeks ago38:43

38:43

Mike Walrath is the CEO and Chairman of Yext, a publicly traded digital presence platform that helps businesses manage and synchronize their digital presence across search engines, maps, apps, and voice assistants by ensuring that information like locations, services, FAQs, and brand content appears accurately and consistently wherever customers search. He also co-founded WGI Group, LLC, to provide growth capital to early and expansion stage startups in enterprise software, consumer internet and digital media industries. Previously, Michael was co-founder and Chairman of Moat Inc. which was acquired by Oracle in April 2017. In 2003, Michael founded Right Media - the world's first open exchange for digital advertising. He served as Chairman and CEO of the company until its acquisition by Yahoo! in July 2007. At Yahoo!, he was responsible for the operation of the global advertising marketplaces organization. Discussed in this Episode: Why marketers must now structure content not for humans, but for machines. How Yext evolved from managing listings to powering AI-ready data pipelines. Actionable steps SaaS companies can take to optimize for AI agents and search diversification. The role of hyperlocal data, competitive analysis, and personalized content in GTM strategy. Why software innovation must start with intelligence, not workflow. The decline of seat-based pricing and rise of outcome-based models. Highlights: [00:07:30] – How the iPhone created geo-aware fragmentation, and how Yext was born. [00:10:00] – Why Google still checks MapQuest (and what that means for SEO today). [00:11:30] – “We have to rebuild the digital presence for machines, not people.” [00:14:30] – The new battleground: how AI engines like ChatGPT shape discoverability. [00:18:00] – Practical data strategies for local businesses and SaaS marketers. [00:22:00] – Why structured data is the foundation of AI-first marketing. [00:26:00] – Bespoke GTM: why no two locations (or campaigns) should be the same. [00:29:00] – The shift from product-led to intelligence-led SaaS development. [00:31:00] – Seat-based pricing is dying – how to move to value-based contracts. [00:34:30] – Mike’s advice: get radically honest about macro changes, not just tactics. Guest Speaker Links (Michael Walrath): LinkedIn: https://www.linkedin.com/in/michael-walrath-b63166/ Yext: https://www.yext.com/ Host Speaker Links (Sophie Buonassisi): LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ Newsletter: https://substack.com/@sophiebuonassisi Where to find GTMnow (GTMfund’s media brand): Website: https://gtmnow.com/ LinkedIn: https://www.linkedin.com/company/gtmnow/ The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

1
GTM 145: What Happens When a CRO Owns the Entire Customer Journey, How to Build a Unified GTM Engine | Marcy Campbell 38:54

5 weeks ago38:54

38:54

Marcy Campbell is the Chief Revenue Officer at AppFolio, where she leads sales and client services with a focus on delivering unified, end-to-end customer experiences. With over 30 years of experience scaling revenue teams across FinTech, SaaS, cloud computing, and communications, Marcy has held executive roles at Boomi and PayPal—where she led an 800+ person global team. Her deep expertise in aligning sales, customer success, and operations makes her a standout leader in the GTM space. What happens when a CRO owns the entire customer journey Discussed in this Episode: How AppFolio’s Unified Customer Experience (UCE) platform aligns marketing, sales, and customer service. The evolving role of the CRO and the importance of owning the entire customer journey. Why customer experience is a competitive differentiator in vertical SaaS. Tactical tips for early-stage startups on aligning go-to-market motion with product-market fit. The importance of cross-functional “stream teams” for accelerating GTM initiatives. How Marcy builds inclusive leadership cultures and mentors rising female leaders. Why how you make the number matters as much as making the number. Highlights: 10:30 The Chief Revenue Officer's (CRO) responsibility to understand and optimize the entire customer journey. 12:30 How the Unified Customer Experience (UCE) platform was formed and how it works. 16:00 End-to-end GTM orchestration across sales, marketing, product, and CS. 22:00 Results from the UCE initiative: accelerated deal velocity and customer retention. 26:30 Advice for startups: identifying your ICP and fixing pipeline fundamentals. 29:00 How to scale with customer empathy and GTM precision. 31:00 Advocating for women in sales leadership and building inclusive teams. 36:00 Marcy’s communication strategy for managing a 600-person org. 39:00 Marcy's favorite business leadership tactic: “Take a beat” before reacting. 40:00 What’s outdated: The belief that only numbers matter in sales. Guest Speaker Links (Marcy Campbell): LinkedIn: https://www.linkedin.com/in/marcyc/ Appfolio: https://www.appfolio.com/ Host Speaker Links (Sophie Buonassisi): LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ Newsletter: https://substack.com/@sophiebuonassisi Where to find GTMnow (GTMfund’s media brand): Website: https://gtmnow.com/ LinkedIn: https://www.linkedin.com/company/gtmnow/ Twitter/X: The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

1
GTM 144: How AI is Rewriting Product and GTM Playbooks | with Oji Udezue (CPO - Typeform, Calendly) 58:30

6 weeks ago58:30

58:30

Oji Udezue was most recently Chief Product Officer at Typeform, where he led product strategy across the company’s growing suite of tools. Previously, he was CPO at Calendly, where he helped scale one of the most beloved PLG tools in the market. Before that, he was Head of Product for Creation and Conversation at Twitter, leading core features like Tweets, DMs, and Spaces. At Atlassian, he led all communication products, including the launch of Atlassian’s first post-IPO product. Oji also spent years at Microsoft, building foundational experiences across Windows, Outlook, Hotmail, and Internet Explorer. In addition to his product leadership, Oji is the founder of Kernel Fund, an early-stage fund supporting startups across Africa. He writes about product, growth, and leadership at his newsletter Product Mind and is the author of the upcoming book Building Rocketships —a guide for high-growth product teams. Discussed in this Episode: When to hire your first PM (and what to look for). Why great product teams include marketing from day one. A framework for picking winning startup ideas. How AI is changing how we build (not just what we build). What product leaders can learn from Microsoft’s Longhorn failure. Why 3x better isn’t a nice-to-have — it’s a must. Highlights: 04:52 – Why marketing is essential to product leadership. 12:02 – How AI is transforming the process of building products. 17:07 – Common product mistakes founders make early on. 24:16 – Building Rocket Ships: Why Oji wrote the book. 31:08 – Framework: Where to fish for unicorns. 33:17 – The “3x better” rule for product value. 37:07 – The challenge of true product differentiation. 39:22 – What Microsoft’s Longhorn failure taught Oji. 44:51 – When (and how) to hire your first PM. 48:31 – The importance of fast, early customer feedback. 54:46 – How AI is changing go-to-market strategy. 57:32 – Why marketers must master signal in a noisy world. Guest Speaker Links (Oji Udezue): LinkedIn: https://www.linkedin.com/in/ojiudezue/ Kernel Fund: https://www.kernelfund.com/ Product Mind: https://www.productmind.co/ Building Rocketships (Book): https://a.co/d/0HGjf18 SubStack: https://ojiudezue.substack.com/ Host Speaker Links (Sophie Buonassisi): LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ Newsletter: https://substack.com/@sophiebuonassisi Where to find GTMnow (GTMfund’s media brand): Website: https://gtmnow.com/ LinkedIn: https: The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

1
GTM 143: Why Most AI Messaging Fails and How to Actually Stand Out in a Crowded Market | Harmony Anderson 37:37

7 weeks ago37:37

37:37

Harmony Anderson is an entrepreneurial marketing leader with deep expertise in building global GTM strategies at growth startups. She is currently the VP of Growth and Marketing at Superhuman, the most productive email app ever made for teams. She has also led high-performing teams at Armada, Engine, Outreach, and ThousandEyes. She is deeply passionate about creating world-class marketing campaigns, leveraging data-driven strategies to accelerate customer acquisition, engagement, and retention. She also drives extreme rigor around operational excellence and efficiency, ensuring GTM teams execute with precision using repeatable and predictable playbooks. Discussed in this Episode: How to develop unique positioning and messaging for an AI company Why UGC matters for your brand and how to get users to create content about your product The impact of lightning marketing campaigns and follow-on 'thunder' campaigns Three core channels for launching a new B2B marketing program Highlights: 05:12 – The #1 mistake in AI messaging: sounding like everyone else. 07:24 – Use outcomes and data to differentiate your AI product. 11:06 – Why nailing 3-5 core use cases beats going broad or too niche. 12:38 – Turning website visitors into believers with demos and interactive content. 14:01 – How to keep up with a market that changes every week (hello, agentic AI). 15:08 – Building campaigns that fuel your narrative across every channel. 17:16 – Behind Superhuman’s most successful campaign ever: “New Year, New Inbox.” 20:04 – Unlocking 60% growth through user-generated content and affiliate advocacy. 21:38 – Why webinars and virtual events still drive real results (and feedback). 23:12 – How to keep your messaging fresh while staying focused. 25:11 – The difference between brand umbrella, campaign, and program — and why it matters. 27:02 – Harmony’s lean, high-impact program playbook for early-stage teams. 31:06 – Building a hype train: how to activate champions at launch. 33:01 – Hot take: marketing shouldn’t be measured by pipeline alone. 35:12 – Why NRR (not just pipeline) should be a marketing KPI. Guest Speaker Links (Harmony Anderson): LinkedIn: linkedin.com/in/harmony-hickman-anderson Superhuman: superhuman.com Host Speaker Links (Sophie Buonassisi): LinkedIn: linkedin.com/in/sophiebuonassisi Newsletter: gtmnow.com/tag/newsletter Where to find GTMnow (GTMfund’s media brand): Website: gtmnow.com LinkedIn: GTMnow X/Twitter: @GTMnow_ YouTube: The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

1
GTM 142: Why Most B2B Marketing Fails (And How to Fix It) with Udi Ledergor 56:47

8 weeks ago56:47

56:47

Udi Ledergor served as CMO during Gong’s rise from new SaaS startup to industry dominance. By building a playful, human-centric brand with a lighthearted tone, he captured buyers’ attention and dollars and turned them into raving fans. He helped Gong go from zero to hundreds of millions in revenue, while achieving a multi-billion-dollar valuation. His book Courageous Marketing is officially out and you can buy it below in the show notes. Discussed in this Episode: Why Marketing 'Best Practices' are broken for Brands that want to stand out. Marketers need to consider the long game and remember the 95/5 rule. When you should hire for experience versus potential. How to foster a culture of healthy risk-taking with your team. Highlights: 04:09 Udi's inspiration for writing his new book, Courageous Marketing. 06:02 The four most common reasons why marketing fails. 09:22 What marketers should be looking for when selecting a company to join. 13:55 The Problem with 'playing it safe' in B2B marketing. 23:07 How to market to both the 5% and the 95% of your buyers. 38:13 The Three Team Operating Principles for leading a bold and effective marketing team. Guest Speaker Links (Udi Ledergor): LinkedIn: https://www.linkedin.com/in/udiledergor/ Gong: https://www.gong.io/ Udi's Book, Courageous Marketing : https://mybook.to/courageousmarketing Host Speaker Links (Sophie Buonassisi): LinkedIn: https://www.linkedin.com/in/sophiebuonassisi/ Newsletter: https://gtmnow.com/tag/newsletter/ Where to find GTMnow (GTMfund’s media brand): Website: https://gtmnow.com/ LinkedIn: https://www.linkedin.com/company/gtmnow/ Twitter/X: https://x.com/GTMnow_ YouTube: / @gtm_now The GTM Podcast (on all major directories): https://gtmnow.com/tag/podcast/ Sponsor: ZoomInfo’s GTM25 Virtual Conference—a free, half-day event on h The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

1
GTM 141: Timeless Growth Tips From a $7.4B Oracle Exit and Scaling Carta to $450M in Revenue | Jeff Perry 50:14

9 weeks ago50:14

50:14

Jeff Perry is a truly iconic revenue leader and the Chief Revenue Officer (CRO) at Carta, responsible for core software revenue across New Business, Upsell, Cross Sell, and Customer Success. Prior to Carta, Jeff led SMB Sales at DocuSign, and started his career at Oracle, where he rose from Strategic Account Manager to VP of Sales over a decade. Discussed in this Episode: How to turn coworkers into mentors—and why it matters. Moving from enterprise sales leadership to a startup environment. Why and when to build a solutions engineering team. The myth of the “18-month CRO lifespan.” Balancing empathy and accountability as a sales leader. Why automation isn’t always the best path forward. Highlights: 06:29 — Mentorship matters. Jeff breaks down how to find and approach mentors—even without a formal program. 12:42 — Lessons from selling servers that still apply to modern SaaS sales 15:02 — Leading through M&A: Inside the culture clash and how Jeff rebuilt a team post-acquisition. 19:07 — Carta’s GTM evolution: How Jeff scaled from one rep selling one product to multiple teams across three business lines. 28:34 — Scaling revenue from $20M to $450M: Advice for CROs entering growth-stage companies. 33:20 — Why “big company” people can thrive in startups—if they leave their playbooks behind. 36:15 — How to use PIPs to coach—not just cut—and what most orgs get wrong. 43:13 — Why the best sellers are quarterbacks, not lone wolves. 46:43 — Pick up the phone: Human connection wins in an era of AI and automation. Guest Links (Jeff Perry): LinkedIn: Jeff Perry Carta: carta.com Host Links (Scott Barker): LinkedIn: Scott Barker Newsletter: The GTM Newsletter Where to Find GTMnow (GTMfund’s Media Brand): Website: gtmnow.com LinkedIn: GTMnow Twitter/X: @GTMnow_ YouTube: @gtm_now Podcast: The GTM Podcast (available on all major platforms) Sponsor: Pursuit The best talent isn’t actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis . As a key GTMfund partner, they equip sales and marketing teams with top performers. If you're hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member. The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

1
GTM 140: How Microsoft Scaled from $600M to $5B: The Enterprise Playbook with Hayden Stafford 54:03

10 weeks ago54:03

54:03

Hayden Stafford is the President and Chief Revenue Officer (CRO) at Seismic, where he oversees the global go-to-market (GTM) organization, including pre-sales, sales, customer success, services, partners, and more. Prior to joining Seismic, he served as President of Global Field Operations at Pegasystems. Before that, Hayden was Corporate Vice President at Microsoft, leading Global Business Applications (Microsoft Dynamics 365) for six years. Earlier in his career, he was an SVP at Salesforce and spent nearly a decade at IBM, ultimately serving as VP and Managing Director on Wall Street. Discussed in this Episode: What Satya Nadella taught Hayden about culture, clarity, and transformation at Microsoft. The exact playbook to move from SMB to enterprise—including partner enablement, segmentation, and incentive design. Why retention isn't just a CS metric—and how to build a sales team that cares about it. How to win in vertical SaaS, from breaking into financial services to owning the category. What it takes to close a $600M+ deal in the middle of a financial crisis. Highlights: 05:19 — How Satya Nadella sold his internal vision and rebuilt Microsoft’s culture from the ground up 13:13 — The partnership blueprint: how to scale with partners, not just transact with them 28:18 — Going deep in verticals: why Seismic dominated financial services while others avoided it 34:44 — How Hayden closed a $600M+ deal with Merrill Lynch after the 2008 crash 42:40 — Why retention should be part of your sales comp—and how to make it work 49:15 — The “Value Continuum”: a framework for aligning sales, services, and CS around business outcomes Guest Speaker Links (Hayden Stafford): LinkedIn: https://www.linkedin.com/in/haydenestafford/ Seismic: https://seismic.com/ Host Speaker Links (Scott Barker): LinkedIn: https://www.linkedin.com/in/ssbarker/ Newsletter: https://thegtmnewsletter.substack.com/ Where to find GTMnow (GTMfund’s media brand): Website LinkedIn Twitter / X YouTube The GTM Podcast (on all major directories) The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

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GTM 139: AI Agents Are Changing Everything — Microsoft’s VP of AI Agents on the New Era of Work and Software | Ray Smith 58:54

11 weeks ago58:54

58:54

Ray Smith is the VP of AI Agents at Microsoft. Previously, he was the Global VP of Product for SAP, CRM and Sales Cloud. Before that, he was the CEO and Co-Founder of DataHug, which was acquired by Calidus Cloud in 2016. Ray breaks down why the rise of AI agents is a tectonic shift, how businesses are already seeing ROI, and what it means for SaaS, team structure, and go-to-market strategies. He also shares real-world use cases from inside Microsoft and partner companies, plus how founders and operators can build or adapt in this new AI-native era. Discussed in this Episode: What exactly is an AI agent—and how is it different from bots or automation? Why traditional SaaS pricing models (like per-seat) don’t work in the agent era. How enterprise teams are already deploying autonomous agents in production. The emerging architecture of multi-agent workflows. Which skills will matter most in an agent-first world (hint: think like a GM or growth hacker). Highlights: 06:53 What makes an AI agent different from bots and automation—and why it matters now. 15:33 How AI agents are changing the role of traditional software tools and UI. 25:15 Why legacy SaaS pricing models don’t work for agents—and what comes next. 31:12 Inside Microsoft CoPilot: Real-world agent use cases across sales, support, and strategy. 37:42 The most valuable skills in the AI era—from delegation to agent orchestration. 51:42 Why agentic AI makes customer relationships and long-term value even more critical. Guest Speaker Links (Ray Smith): LinkedIn: https://www.linkedin.com/in/raycsmith/ Host Speaker Links (Scott Barker): LinkedIn: https://www.linkedin.com/in/ssbarker/ Newsletter: https://thegtmnewsletter.substack.com/ Where to find GTMnow (GTMfund’s media brand): Website: https://gtmnow.com/ LinkedIn: https://www.linkedin.com/company/gtmnow/ Twitter/X: https://x.com/GTMnow_ YouTube: / @gtm_now The GTM Podcast (on all major directories): The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

1
GTM 138: The AI Advantage, Solving Sales & Marketing Alignment for Better GTM Execution with Jaleh Rezaei 54:23

12 weeks ago54:23

54:23

Jaleh Rezaei is the CEO & Co-founder of Mutiny, a company reimagining the B2B buying experience by transforming transactional relationships into meaningful connections through AI-powered personalization. Mutiny helps enterprises restore the human element in modern buying at scale, and is used by some of the fastest growing companies in the world including Amplitude, Snowflake and Qualtrics. The company is backed by Sequoia Capital, Tiger Global, and CMOs of companies such as Uber, Condé Nast and Salesforce. Prior to Mutiny, Jaleh was the Head of Marketing and Business Development at Gusto, where she grew the company from 500 to 50,000 customers over 4 years. She was the Director of Product Marketing at VMware prior to Gusto. Discussed in this Episode: AI-powered personalization is reshaping B2B sales and marketing AI-driven lead scoring improves quality and targets high-value prospects AI anticipates and overcomes sales objections in real time Sales & marketing alignment: why it matters and how to achieve it The risks of AI-driven outbound and how to avoid common pitfalls Scaling 1:1 experiences efficiently with AI AI-powered buyer interactions and their impact on GTM strategies Highlights: 03:27 – Why AI innovation is game-changing for founders building and scaling companies. 06:49 – How 1:1 sales personalization drives 14x higher conversion rates. 10:45 – AI-powered hyper-personalization is reshaping enterprise sales. 16:30 – The biggest AI mistakes in sales and marketing. 20:55 – Scaling white-glove experiences across all target accounts. 24:45 – Why CRM data is a mess and how AI finally fixes it. 28:14 – A masterclass in sales & marketing alignment. 31:20 – The real reason sales and marketing clash (and how to fix it). 42:10 – The most valuable AI use cases for B2B sales teams. 47:30 – How AI is changing B2B buyer behavior and what sellers must do. Guest Speaker Links (Jaleh Rezaei): LinkedIn: https://www.linkedin.com/in/jalehr/ Mutiny: https://www.mutinyhq.com/ The State of Sales & Marketing Alignment Report: https://www.mutinyhq.com/report Host Speaker Links (Scott Barker): LinkedIn: https://www.linkedin.com/in/ssbarker/ Newsletter: https://thegtmnewsletter.substack.com/ Find GTMnow (GTMfund’s Media Brand): Website LinkedIn Twitter/X [YouTube]( / @gtm_now) Podcast The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

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GTM 137: The Biggest Business Turnaround You've Never Heard Of & The Growth Levers to Pull When Things Go Wrong | Cassie Young 56:24

13 weeks ago56:24

56:24

Cassie Young is a General Partner at Primary Venture Partners, a $1B AUM early-stage venture capital firm in New York that has backed category-defining companies such as Chief, Alma, K Health, Latch, Alloy, Dandy and Vestwell. Before joining Primary, Cassie was Chief Customer and Commercial Officer for Marigold (formerly known as CM Group), an Insight Partners roll-up of marketing technology software including Sailthru, Campaign Monitor, Delivra, Emma, Vuture and Liveclicker; Cassie assumed that role when Marigold acquired Sailthru, where she was Chief Revenue Officer. Prior to Sailthru, Cassie served as VP Marketing & Analytics at Gerson Lehrman Group ("GLG") and as VP Marketing & Growth for Savored (acquired by Groupon). Cassie's time in tech dates back to 2006, when she joined TheLadders.com as an early employee and managed marketing and analytics for the company's subscription business. She began her career as a tech and media analyst at Citigroup Global Corporate & Investment Bank. Discussed in this Episode: The turnaround story of Cassie’s time at Sailthru and overcoming scaling challenges. How to rebuild and regain customer trust after technical failures. The importance of leadership alignment and transparency during times of crisis. How to effectively use Net Promoter Score (NPS) and what it really tells you. The value and impact of Customer Advisory Boards (CABs) in driving customer-centric growth. Why executive compensation should align with key business metrics for better team alignment. Creative tactics like video mailers and regional user groups to engage customers and drive product adoption. Highlights: 07:53 What happens when commercial scale outgrows your technical scale. 15:53 Driving alignment through northstar metrics and incentives. 22:16 The best ways to measure customer trust. 34:10 Tips on setting up a Customer Advisory Board (CAB). 52:48 A fantastic multi-media mail campaign. Guest Speaker (Cassie Young): LinkedIn Primary VC Host (Scott Barker): LinkedIn Newsletter Find GTMnow (GTMfund’s Media Brand): Website LinkedIn Twitter/X [YouTube]( / @gtm_now) Podcast Sponsor: Pursuit The best talent isn’t actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis . As a key GTMfund partner, they equip sales and marketing teams with top performers. If you're hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member. The GTM Podcast The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth. Visit gtmnow.com for more episodes and other interesting content.…

The GTM Podcast

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GTM 136: How Asana & Calendly Scaled: PLG to SLG Playbooks That Work | Jessica Gilmartin 59:07

14 weeks ago59:07