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Dale Dupree: Rebellion, Reflection, and the AI Debate
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In this special debrief episode of Make It Happen Mondays, John Barrows sits down with Dale Dupree—founder of The Sales Rebellion and one of the standout voices from the recent Sales Play event in NYC. What starts as a post-event reflection quickly turns into a deep, unfiltered conversation on modern sales, personal transformation, and cultural shifts in the industry.Dale and John unpack the bold themes and subtle symbolism behind Glengarry Glen Ross, from gender and race dynamics to toxic sales archetypes. They also explore why Dale believes we’ve lost the “benefit of the doubt” in society—and why it’s time to bring empathy back into business. They also dive into a spicy moment where Dale called AI a “trend”… and the room nearly exploded.This one is raw, thoughtful, and 100% Rebellion. Buckle up.
Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together!
Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/
Connect with John on IG: https://www.instagram.com/johnmbarrows/
Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1
Join John's Newsletter: https://www.jbarrows.com/newsletter
Connect with Dale on LinkedIn: https://www.linkedin.com/in/copierwarrior/
Check out Dale's Websites: crumpledletter.com, thesalesrebellion.com, and copierwarrior.com
271 episodes
ShareManage episode 476965898 series 2509884
Content provided by John Barrows. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by John Barrows 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.
In this special debrief episode of Make It Happen Mondays, John Barrows sits down with Dale Dupree—founder of The Sales Rebellion and one of the standout voices from the recent Sales Play event in NYC. What starts as a post-event reflection quickly turns into a deep, unfiltered conversation on modern sales, personal transformation, and cultural shifts in the industry.Dale and John unpack the bold themes and subtle symbolism behind Glengarry Glen Ross, from gender and race dynamics to toxic sales archetypes. They also explore why Dale believes we’ve lost the “benefit of the doubt” in society—and why it’s time to bring empathy back into business. They also dive into a spicy moment where Dale called AI a “trend”… and the room nearly exploded.This one is raw, thoughtful, and 100% Rebellion. Buckle up.
Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together!
Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/
Connect with John on IG: https://www.instagram.com/johnmbarrows/
Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1
Join John's Newsletter: https://www.jbarrows.com/newsletter
Connect with Dale on LinkedIn: https://www.linkedin.com/in/copierwarrior/
Check out Dale's Websites: crumpledletter.com, thesalesrebellion.com, and copierwarrior.com
271 episodes
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Alyssa Merwin: Inside LinkedIn’s $1B Sales Engine 54:13
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Play Later Play Later Lists Like LikedIn this episode, John Barrows is joined with with Alyssa Merwin , Global VP of LinkedIn Sales Solutions, to unpack the findings from LinkedIn’s brand-new ROI of AI Report —a first-of-its-kind look at how AI is truly impacting sales outcomes, not just activity metrics.With over $1 billion in revenue under her leadership and a rich career path shaped by EQ, adaptability, and grit, Alyssa shares how she’s guiding one of the most innovative sales organizations in tech. The conversation dives into her journey from a liberal arts background to sales leadership, her time at Corporate Executive Board (home of The Challenger Sale ), and what she’s seeing as the biggest shifts in modern selling.The takeaway? If you’re not using AI in your sales process every day , you’re falling behind. This episode is a wake-up call—packed with insights, data, and leadership wisdom from one of the top voices in the industry. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Alyssa on LinkedIn: https://www.linkedin.com/in/alyssa1/…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Sam Jacobs: Community, Character, and the Future of Leadership 56:50
56:50 Play Later Play Later Lists Like Liked56:50
Play Later Play Later Lists Like LikedJohn Barrows reconnects with longtime friend and Pavilion CEO, Sam Jacobs. Sam is the author of the bestselling book Kind Folks Finish First , and he’s on a mission to prove that building with integrity and empathy isn’t just good for the soul—it’s good for business.John and Sam dive into the hard lessons learned from the rollercoaster ride of 2023, how timing and positioning can humble even the best ideas, and why leading with values matters more than ever. They also break down the evolving role of the CRO in today’s AI-driven world, the power of community, and how authenticity is becoming the new competitive edge.This conversation is real, reflective, and packed with insight for anyone trying to do good business—without losing their soul in the process. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Sam on LinkedIn: https://www.linkedin.com/in/samfjacobs/ Check out Sam's Website: https://www.joinpavilion.com/…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Kevin Evers: Taylor Swift’s Masterclass in Brand, Loyalty & Strategy 54:25
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Play Later Play Later Lists Like LikedKevin Evers is a senior editor at Harvard Business Review and author of the upcoming book There’s Nothing Like This: The Strategic Genius of Taylor Swift . In this episode, Kevin and John break down what makes Taylor Swift one of the most brilliant business minds of our time. From reclaiming her masters to building an unbreakable bond with fans, Swift’s ability to scale the unscalable, adapt to change, and maintain authenticity offers powerful lessons for sales, leadership, and entrepreneurship. Whether you’re a Swiftie or not, this conversation is packed with insights on vision, branding, and long-term success. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Kevin on LinkedIn: https://www.linkedin.com/in/kevin-evers1/ Connect with Kevin on IG: https://www.instagram.com/there_is_nothing_like_this/ Get Kevin's Book: https://www.amazon.com/Theres-Nothing-Like-This-Strategic/dp/B0DD2XL7C5…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Dale Dupree: Rebellion, Reflection, and the AI Debate 58:40
58:40 Play Later Play Later Lists Like Liked58:40
Play Later Play Later Lists Like LikedIn this special debrief episode of Make It Happen Mondays , John Barrows sits down with Dale Dupree—founder of The Sales Rebellion and one of the standout voices from the recent Sales Play event in NYC. What starts as a post-event reflection quickly turns into a deep, unfiltered conversation on modern sales, personal transformation, and cultural shifts in the industry.Dale and John unpack the bold themes and subtle symbolism behind Glengarry Glen Ross , from gender and race dynamics to toxic sales archetypes. They also explore why Dale believes we’ve lost the “benefit of the doubt” in society—and why it’s time to bring empathy back into business. They also dive into a spicy moment where Dale called AI a “trend”… and the room nearly exploded.This one is raw, thoughtful, and 100% Rebellion. Buckle up. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Dale on LinkedIn: https://www.linkedin.com/in/copierwarrior/ Check out Dale's Websites: crumpledletter.com , thesalesrebellion.com , and copierwarrior.com…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 The Sales Play: Glengarry Glen Ross After Hours 45:25
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Play Later Play Later Lists Like LikedIn this special Make It Happen Mondays episode, John Barrows takes you inside an intimate, after-hours debrief unlike anything we’ve released before. After a full day of sales content, networking, and roundtable discussions in NYC with 18 of the top minds in sales and tech, the group capped the night with a viewing of the Broadway revival of Glengarry Glen Ross , starring Bill Burr, Kieran Culkin, and Bob Odenkirk. What followed was a raw, insightful, and unfiltered conversation back at John’s suite—covering everything from the timeless truths (and toxic flaws) of classic sales culture, to modern reflections on gender, race, authenticity, and the future of our profession.Featuring Jeff Hoffman, Morgan J Ingram, Doug Landis, J. Ryan Williams, Ashley Welch, Stefanie Boyer, Jaime Diglio, Sara Uy, Roderick Jefferson, Kasey Jones, Jen Igartua, Aneesh Lal, and more—this is your Sales MBA , served with bourbon and brutal honesty.You’ve never heard a sales conversation like this before. Buckle up. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 The Only Authenticated Episode Ever – Featuring Drift’s David Cancel 1:14:15
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Play Later Play Later Lists Like LikedIn this special crossover episode, John Barrows is joined by Doug Landis and Jen Allen-Knuth for the one and only recorded session of a pilot project called Authenticated —a podcast experiment designed around unscripted, authentic conversations with inspiring leaders.The guest? None other than David Cancel, Founder and former CEO of Drift. David drops incredible insight on sales, marketing, leadership, and strategy—backed by decades of hard-won experience. If you’ve ever wondered what it’s like to learn directly from one of the best in the business, this is that moment. This is Authenticated . Unfiltered. Unpolished. Unmissable. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with David Cancel on LinkedIn: https://www.linkedin.com/in/dcancel/…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Steve Lucas: Why AI Won’t Replace You—Unless You Let It 56:22
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Play Later Play Later Lists Like LikedSteve Lucas is a seasoned enterprise software executive and the CEO of Boomi, leading AI-driven digital transformation. In this episode, he and John Barrows dive deep into the evolving role of AI in business, sales, and leadership.They explore insights from Steve’s book, Digital Impact: The Human Element of AI-Driven Tech Transformation , and discuss how AI can actually bring back human connection instead of replacing it. Steve shares why companies and professionals must integrate AI into every aspect of their work—and what happens if they don’t. If you’re wondering how to stay relevant in an AI-powered world, this is the conversation you need to hear. Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Steve on LinkedIn: https://www.linkedin.com/in/nstevenlucas/ Get Steve's book here: https://boomi.com/content/digital-impact-affiliate-pre-order/…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Larry Kim: Scaling Sales with a Product-First Mindset 56:57
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Play Later Play Later Lists Like LikedLarry Kim is the founder and CEO of Customers.ai and the visionary behind WordStream, which he scaled to a $150M exit. In this episode, John and Larry dive into the battle between product-driven growth and go-to-market strategy, exploring why Larry believes a strong product trumps traditional sales tactics.Larry shares lessons from scaling two companies, including his experience hiring (and firing) sales leaders, the power of founder-led sales, and how he slimmed down his team while tripling revenue. If you’re building a business, selling in a competitive space, or struggling with product-market fit, this episode is packed with game-changing insights. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Larry on LinkedIn: https://www.linkedin.com/in/larrykim/ Check out Larry's Website: https://customers.ai/…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 John Shulman: Winning with Interest-Based Negotiation 57:57
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Play Later Play Later Lists Like LikedJohn Shulman is the Founder and President of Alignor, a negotiation expert with Harvard credentials, and a consultant to business leaders worldwide. This episode is all about the art of negotiation—from handling tough procurement conversations to defending price in a world of price-focused buyers.Learn about the interest-based negotiation approach, where it aligns (or conflicts) with today’s high-stakes sales environment, and how AI is reshaping the way we negotiate. If you are looking for sharpen your negotiation skills and close better deals real with world strategies and insights, this episode is a must-listen. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with John Shulman on LinkedIn: https://www.linkedin.com/in/john-shulman-1b12202/? Check out John Shulman's Website: https://www.alignor.com/…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Elina Teboul: Rethinking Capitalism with Feminine Intelligence 1:13:06
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Play Later Play Later Lists Like LikedElina Teboul is a leadership expert, former attorney, and author of Feminine Intelligence: How Visionary Leaders Can Reshape Business for Good . In this episode, Elina and John dive deep into the balance between logic and empathy in leadership, the flaws in modern capitalism, and how embracing feminine intelligence —not feminism—can drive business success. They discuss the importance of values, “awake” capitalism vs. “woke” capitalism, and how businesses can thrive by integrating emotional intelligence with traditional business strategy. Plus, they explore AI’s potential impact on leadership and the future of work. This conversation is a wake-up call for anyone looking to lead with impact. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Elina on LinkedIn: https://www.linkedin.com/in/elinateboul/ Connect with Elina on IG: https://www.instagram.com/elinateboul/ Check out Elina's Websites: https://elinateboul.com/ and https://feminineintelligencebook.com/…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Shari Dunn: Uncovering Bias and Redefining Competency at Work 1:15:07
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Play Later Play Later Lists Like LikedShari Dunn is a polymath—an accomplished journalist, attorney, CEO, news anchor, and university professor—who brings a wealth of experience to this powerful conversation. She joins John Barrows to discuss her book, QUALIFIED: How Competency Checking and Race Collide at Work. Shari explores the hidden biases in hiring and promotion, the concept of “competency checking,” and the importance of seeing diversity, equity, and inclusion (DEI) as a strategic imperative for business success. This insightful conversation offers actionable steps for redefining how we evaluate talent and building workplaces where everyone can thrive. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Shari on LinkedIn: https://www.linkedin.com/in/sharidunn Check out Shari's Website: https://thesharidunn.com Connect with Shari on IG: https://www.instagram.com/thesharidunn.com6/ Order Shari’s book, Qualified : https://thesharidunn.com/buy-now…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Sydney Sloan: CMO Insights and Intent 1:13:01
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Play Later Play Later Lists Like LikedSydney Sloan is a seasoned marketing leader and the CMO at G2, the world’s largest software marketplace. In this episode John and Sydney discuss the evolving relationship between sales and marketing, the rise of AI, and how businesses can stay ahead. Sydney shares her personal experience with burnout, the importance of energy management, and how taking a step back helped her gain fresh perspectives. They also dive into AI-driven intent data, hyper-personalization, and what sales reps must do to stay relevant in an ever-changing landscape. If you want to future-proof your sales and marketing strategy, this is a must-listen conversation! Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Sydney on LinkedIn: https://www.linkedin.com/in/sydsloan/ Check out G2's Website: https://www.g2.com/…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Partnership ANNOUNCEMENT: Zero-to-Pipeline in 60 Days with Alex Buckles 54:27
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Play Later Play Later Lists Like LikedAlex Buckles is back! As the CEO of Forecastable, Alex helps sales teams drive more qualified leads by tapping into their partner networks. In this episode, John and Alex dive deep into the tactical strategies reps and sales leaders can use to activate their company’s ecosystem—partners, investors, advisors, and employees—to generate real revenue.John is so impressed with Alex’s approach that he’s incorporating it into his own strategy and launching a free webinar on February 20th to help sales teams start seeing results within 60 days. This conversation is packed with actionable insights—if you want to differentiate yourself and drive sales through partnerships, don’t miss it! Check the show notes for webinar details. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! SIGNUP TO THE WEBINAR: https://my.demio.com/ref/8sxvVCvt8n1REFrI Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Alex on LinkedIn: https://www.linkedin.com/in/alexbuckles/ Check out Alex's Website: https://forecastable.com…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Jonathan Lister: Building Billion-Dollar Organizations with Curiosity 54:41
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Play Later Play Later Lists Like LikedJohn Barrows is joined by Jonathan Lister, COO of Vidyard and former VP of Global Sales Solutions at LinkedIn. With over 25 years of experience in B2B tech and SaaS, Jonathan shares his journey of building billion-dollar organizations and explains the critical role of curiosity in leadership and hiring.Jonathan breaks down the evolving role of sales in the AI era, emphasizing the shift from quantity to quality in personalized selling. If you’re ready to unlock talent, embrace change, and shape the future of sales, this conversation is packed with actionable insights. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Jonathan on LinkedIn: https://www.linkedin.com/in/jonathanlister/ Check out the Vidyard Website: https://www.vidyard.com/…
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Make It Happen Mondays - B2B Sales Talk with John Barrows
1 Alex Newmann: Breaking Free from Founder-Led Sales 1:00:26
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Play Later Play Later Lists Like LikedJohn Barrows sits down with Alex Newmann, founder and CEO of Newmann Consulting Group. Alex specializes in helping B2B companies transition from founder-led sales to scalable, repeatable sales systems. Together, they unpack the challenges founders face when building a sales team, share actionable strategies for avoiding common pitfalls, and discuss the realities of entrepreneurship. If you’re a founder looking to scale your business, this is the must-listen conversation to kickstart your journey. Are you interested in leveling up your sales skills and staying relevant in today’s AI-driven landscape? Visit www.jbarrows.com and let’s Make It Happen together! Connect with John on LinkedIn: https://www.linkedin.com/in/johnbarrows/ Connect with John on IG: https://www.instagram.com/johnmbarrows/ Check out John's Membership: https://go.jbarrows.com/pages/individual-membership?ref=3edab1 Join John's Newsletter: https://www.jbarrows.com/newsletter Connect with Alex on LinkedIn: https://www.linkedin.com/in/alexnewmann/ Check out Alex's Websites: https://www.alexnewmann.com/ and https://victoryhub.io/…
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