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The GTM Reckoning: AI, Job Security, and Why Leaders Are Falling Behind
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.
In this episode, I sit down with Sam Jacobs, founder of Pavilion, to unpack the seismic shifts shaking SaaS leadership:
Why growth has never been harder — even at top-tier tech companies
The coming retention crisis for AI-native businesses
How Pavilion grew from a small dinner club into the SaaS industry’s barometer
Why showing up, doing things that don’t scale, and telling a story are now non-negotiable
The uncomfortable truth about job security and running outdated GTM playbooks
If you’re a founder, operator, or executive trying to navigate the future of GTM, this conversation is for you.
Listen, take notes, and figure out how to stay ahead before it’s too late.
👇 Timestamps & Resources below 👇00:00 Trailer – The GTM Reckoning: AI, Power Shifts, and What’s Breaking in SaaS00:54 Why AI-Native Companies Aren’t Playing the Efficiency Game – A Tale of Two Worlds05:18 Why Growth Is So Hard Right Now & Why There’s No Job Security for GTM Execs — Even at Elite Tech Companies09:30 Drivers vs. Passengers – Why So Many GTM Leaders Are Running Outdated, Dumb Playbooks13:30 The Pavilion Origin Story – From a Small Dinner Club to the SaaS Industry’s Unofficial Barometer21:08 “The Road to Hell Is Paved With Good Intentions” – Why You Can’t Build an Exclusive Community and Be Fully Inclusive at the Same Time27:00 The Power of Doing Things That Don’t Scale – Why Showing Up Daily and Being Face-to-Face With the Market Still Wins39:00 The Coming Retention Apocalypse for AI-Native Companies & Why Harry Stebbings’ Incentives Aren’t Aligned With Yours44:32 Are ChatGPT Prompts Actually Well-Intentioned? Or Are They Engineered for Addiction and Product Dependency?47:00 What AI Adoption Really Means for GTM Leaders & How the Role of Executives Is About to Change53:00 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: / samfjacobs 🎧 Topline Podcast: • E120: What does the future of tech look li... 🎙 The Heresy Podcast – conversations with builders, thinkers & rebels 🔔 Subscribe: / @heresypodcast 📱The Heresy Pod on Instagram: / heresy.pod 🔗 Follow Dimitar: https://www.linkedin.com/in/stanimiroff/
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By Dimitar Stanimiroff2023 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.
In this episode, I sit down with Sam Jacobs, founder of Pavilion, to unpack the seismic shifts shaking SaaS leadership:
Why growth has never been harder — even at top-tier tech companies
The coming retention crisis for AI-native businesses
How Pavilion grew from a small dinner club into the SaaS industry’s barometer
Why showing up, doing things that don’t scale, and telling a story are now non-negotiable
The uncomfortable truth about job security and running outdated GTM playbooks
If you’re a founder, operator, or executive trying to navigate the future of GTM, this conversation is for you.
Listen, take notes, and figure out how to stay ahead before it’s too late.
👇 Timestamps & Resources below 👇00:00 Trailer – The GTM Reckoning: AI, Power Shifts, and What’s Breaking in SaaS00:54 Why AI-Native Companies Aren’t Playing the Efficiency Game – A Tale of Two Worlds05:18 Why Growth Is So Hard Right Now & Why There’s No Job Security for GTM Execs — Even at Elite Tech Companies09:30 Drivers vs. Passengers – Why So Many GTM Leaders Are Running Outdated, Dumb Playbooks13:30 The Pavilion Origin Story – From a Small Dinner Club to the SaaS Industry’s Unofficial Barometer21:08 “The Road to Hell Is Paved With Good Intentions” – Why You Can’t Build an Exclusive Community and Be Fully Inclusive at the Same Time27:00 The Power of Doing Things That Don’t Scale – Why Showing Up Daily and Being Face-to-Face With the Market Still Wins39:00 The Coming Retention Apocalypse for AI-Native Companies & Why Harry Stebbings’ Incentives Aren’t Aligned With Yours44:32 Are ChatGPT Prompts Actually Well-Intentioned? Or Are They Engineered for Addiction and Product Dependency?47:00 What AI Adoption Really Means for GTM Leaders & How the Role of Executives Is About to Change53:00 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: / samfjacobs 🎧 Topline Podcast: • E120: What does the future of tech look li... 🎙 The Heresy Podcast – conversations with builders, thinkers & rebels 🔔 Subscribe: / @heresypodcast 📱The Heresy Pod on Instagram: / heresy.pod 🔗 Follow Dimitar: https://www.linkedin.com/in/stanimiroff/