<p>2023 broke the old rules of go-to-market. AI isn’t just changing the tools — it’s rewriting the entire playbook, and most GTM leaders are already behind.</p><p><br></p><p>In this episode, I sit down with <strong>Sam Jacobs</strong>, founder of Pavilion, to unpack the seismic shifts shaking SaaS leadership:</p><ul><li><p>Why growth has never been harder — even at top-tier tech companies</p></li><li><p>The coming retention crisis for AI-native businesses</p></li><li><p>How Pavilion grew from a small dinner club into the SaaS industry’s barometer</p></li><li><p>Why showing up, doing things that don’t scale, and telling a story are now non-negotiable</p></li><li><p>The uncomfortable truth about job security and running outdated GTM playbooks</p></li></ul><p>If you’re a founder, operator, or executive trying to navigate the future of GTM, this conversation is for you.</p><p><strong>Listen, take notes, and figure out how to stay ahead before it’s too late.</strong></p><p><br></p><p>👇 Timestamps &amp; Resources below 👇<a href="https://www.youtube.com/watch?v=06ZThmycFAA">00:00</a> Trailer – The GTM Reckoning: AI, Power Shifts, and What’s Breaking in SaaS<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=54s">00:54</a> Why AI-Native Companies Aren’t Playing the Efficiency Game – A Tale of Two Worlds<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=318s">05:18</a> Why Growth Is So Hard Right Now &amp; Why There’s No Job Security for GTM Execs — Even at Elite Tech Companies<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=570s">09:30</a> Drivers vs. Passengers – Why So Many GTM Leaders Are Running Outdated, Dumb Playbooks<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=810s">13:30</a> The Pavilion Origin Story – From a Small Dinner Club to the SaaS Industry’s Unofficial Barometer<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=1268s">21:08</a> “The Road to Hell Is Paved With Good Intentions” – Why You Can’t Build an Exclusive Community and Be Fully Inclusive at the Same Time<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=1620s">27:00</a> The Power of Doing Things That Don’t Scale – Why Showing Up Daily and Being Face-to-Face With the Market Still Wins<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=2340s">39:00</a> The Coming Retention Apocalypse for AI-Native Companies &amp; Why Harry Stebbings’ Incentives Aren’t Aligned With Yours<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=2672s">44:32</a> Are ChatGPT Prompts Actually Well-Intentioned? Or Are They Engineered for Addiction and Product Dependency?<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=2820s">47:00</a> What AI Adoption Really Means for GTM Leaders &amp; How the Role of Executives Is About to Change<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=3180s">53:00</a> Why Storytelling and a Strong Point of View Matter More Than Ever In a World Where Everyone Has the Same Tools🔔 Don’t forget to subscribe for more unfiltered convos on technology, arts, and defying the status quo.Follow Sam:🔗 LinkedIn: <a href="https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa3VzRVRzcHE2UWN4MVFGX01rT09XeTJwYjdMd3xBQ3Jtc0tuNkhLdEMzVEtPVnNVRG1hbGNwNlFwQXlVdmxoR2J5dW5WVmRvbS1hR25EYzYxOHQyZjYtZkl1XzlqanJKcTdYWHQ2Y3BlV1NxemZOT1RHejBUUXZKT29SeW5aSnZ4RFVvcFJzNlRHUUd0aW5ZSWRwTQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fsamfjacobs%2F&v=06ZThmycFAA" target="_blank" rel="nofollow">  / samfjacobs  </a> 🎧 Topline Podcast: <a href="https://www.youtube.com/watch?v=Cpw2pkq-FXI&list=PLhQcRYwr2o1OYSZtFd3oGTNRYSoBaxibr&index=1">   • E120: What does the future of tech look li...  </a> 🎙 The Heresy Podcast – conversations with builders, thinkers &amp; rebels 🔔 Subscribe:  / @heresypodcast   📱The Heresy Pod on Instagram: <a href="https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbmZJMXJSYkdBLWJ0ZnduekhmeEhIU2lnTmNpd3xBQ3Jtc0ttbGt1V0VrSlVYaU91UnVZRnpQT1c5WDR3d01ONkpvMjZxUDdOYTRHMkpYcHZSYTBUajdKUndBc3Rfa1g3T2JEbXE5eVBUVkJkTXdKZFJ4Ri1xWUZqV0M5aTJfRjRTaHhxSHBSX2JYdm42Y05vMExFMA&q=https%3A%2F%2Fwww.instagram.com%2Fheresy.pod&v=06ZThmycFAA" target="_blank" rel="nofollow">  / heresy.pod  </a>🔗 Follow Dimitar:   https://www.linkedin.com/in/stanimiroff/</p>

Heresy

Dimitar Stanimiroff

The GTM Reckoning: AI, Job Security, and Why Leaders Are Falling Behind

DEC 18, 202559 MIN
Heresy

The GTM Reckoning: AI, Job Security, and Why Leaders Are Falling Behind

DEC 18, 202559 MIN

Description

<p>2023 broke the old rules of go-to-market. AI isn’t just changing the tools — it’s rewriting the entire playbook, and most GTM leaders are already behind.</p><p><br></p><p>In this episode, I sit down with <strong>Sam Jacobs</strong>, founder of Pavilion, to unpack the seismic shifts shaking SaaS leadership:</p><ul><li><p>Why growth has never been harder — even at top-tier tech companies</p></li><li><p>The coming retention crisis for AI-native businesses</p></li><li><p>How Pavilion grew from a small dinner club into the SaaS industry’s barometer</p></li><li><p>Why showing up, doing things that don’t scale, and telling a story are now non-negotiable</p></li><li><p>The uncomfortable truth about job security and running outdated GTM playbooks</p></li></ul><p>If you’re a founder, operator, or executive trying to navigate the future of GTM, this conversation is for you.</p><p><strong>Listen, take notes, and figure out how to stay ahead before it’s too late.</strong></p><p><br></p><p>👇 Timestamps &amp; Resources below 👇<a href="https://www.youtube.com/watch?v=06ZThmycFAA">00:00</a> Trailer – The GTM Reckoning: AI, Power Shifts, and What’s Breaking in SaaS<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=54s">00:54</a> Why AI-Native Companies Aren’t Playing the Efficiency Game – A Tale of Two Worlds<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=318s">05:18</a> Why Growth Is So Hard Right Now &amp; Why There’s No Job Security for GTM Execs — Even at Elite Tech Companies<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=570s">09:30</a> Drivers vs. Passengers – Why So Many GTM Leaders Are Running Outdated, Dumb Playbooks<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=810s">13:30</a> The Pavilion Origin Story – From a Small Dinner Club to the SaaS Industry’s Unofficial Barometer<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=1268s">21:08</a> “The Road to Hell Is Paved With Good Intentions” – Why You Can’t Build an Exclusive Community and Be Fully Inclusive at the Same Time<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=1620s">27:00</a> The Power of Doing Things That Don’t Scale – Why Showing Up Daily and Being Face-to-Face With the Market Still Wins<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=2340s">39:00</a> The Coming Retention Apocalypse for AI-Native Companies &amp; Why Harry Stebbings’ Incentives Aren’t Aligned With Yours<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=2672s">44:32</a> Are ChatGPT Prompts Actually Well-Intentioned? Or Are They Engineered for Addiction and Product Dependency?<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=2820s">47:00</a> What AI Adoption Really Means for GTM Leaders &amp; How the Role of Executives Is About to Change<a href="https://www.youtube.com/watch?v=06ZThmycFAA&t=3180s">53:00</a> Why Storytelling and a Strong Point of View Matter More Than Ever In a World Where Everyone Has the Same Tools🔔 Don’t forget to subscribe for more unfiltered convos on technology, arts, and defying the status quo.Follow Sam:🔗 LinkedIn: <a href="https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqa3VzRVRzcHE2UWN4MVFGX01rT09XeTJwYjdMd3xBQ3Jtc0tuNkhLdEMzVEtPVnNVRG1hbGNwNlFwQXlVdmxoR2J5dW5WVmRvbS1hR25EYzYxOHQyZjYtZkl1XzlqanJKcTdYWHQ2Y3BlV1NxemZOT1RHejBUUXZKT29SeW5aSnZ4RFVvcFJzNlRHUUd0aW5ZSWRwTQ&q=https%3A%2F%2Fwww.linkedin.com%2Fin%2Fsamfjacobs%2F&v=06ZThmycFAA" target="_blank" rel="nofollow">  / samfjacobs  </a> 🎧 Topline Podcast: <a href="https://www.youtube.com/watch?v=Cpw2pkq-FXI&list=PLhQcRYwr2o1OYSZtFd3oGTNRYSoBaxibr&index=1">   • E120: What does the future of tech look li...  </a> 🎙 The Heresy Podcast – conversations with builders, thinkers &amp; rebels 🔔 Subscribe: / @heresypodcast 📱The Heresy Pod on Instagram: <a href="https://www.youtube.com/redirect?event=video_description&redir_token=QUFFLUhqbmZJMXJSYkdBLWJ0ZnduekhmeEhIU2lnTmNpd3xBQ3Jtc0ttbGt1V0VrSlVYaU91UnVZRnpQT1c5WDR3d01ONkpvMjZxUDdOYTRHMkpYcHZSYTBUajdKUndBc3Rfa1g3T2JEbXE5eVBUVkJkTXdKZFJ4Ri1xWUZqV0M5aTJfRjRTaHhxSHBSX2JYdm42Y05vMExFMA&q=https%3A%2F%2Fwww.instagram.com%2Fheresy.pod&v=06ZThmycFAA" target="_blank" rel="nofollow">  / heresy.pod  </a>🔗 Follow Dimitar: https://www.linkedin.com/in/stanimiroff/</p>