That’s the biggest takeaway from my recent conversation with Zach Vidor, CEO of Octave, on Playbook Broken. We covered a lot of ground, but one theme kept circling back: the old go-to-market (GTM) playbooks aren’t failing because they were bad. They’re failing because the game changed, and we’re still pretending the field looks the same.

Octave’s philosophy that “outbound isn’t broken, your playbook is,” isn’t just a cheeky line. It’s a diagnosis. The explosion of generative AI, the collapse of traditional moats, and the accelerating entropy in tech markets have outpaced how most companies align teams, build messaging, and respond to signals.

Zach calls it Generative GTM — a rethink of how core messaging, ICP definition, and positioning are created, not just executed. The goal isn’t automation. It’s contextual intelligence. An always-on feedback loop between what you say, who hears it, and how they respond.

A few things stuck with me:

* Growth isn’t easy — and never will be. The promise of “easy button” AI is seductive, but dangerous. Strategy still matters. Judgment still matters. And storytelling? Still king. Growth is harder than ever. Get over it.

* The battlefield has shifted. Feature moats are gone. Everyone has access to the same code, same tools, same speed. Your story, how you explain what you do and why it matters, is now the primary differentiator.

* Marketing and sales must operate like SEAL Team Six. No more annual kickoffs with quarterly updates. We need integrated, real-time feedback loops across the funnel. A single, fluid team. Get it together, people!

* Metrics don’t tell the full story anymore. Execs don’t need more dashboards. They need synthesized signals: what personas care about, how narratives are landing, and what needs to change. And they need it fast.

This isn’t about hype. It’s about adaptation. Most companies still measure the world with yesterday’s tools, while their buyers move faster, are harder to reach, and expect more precision.

If we want to survive the coming wave of agentic workflows, synthetic buyers, and infinite niche competition, we can’t just retool the old playbook. We have to rebuild the operating system.

And we have to do it now.

Curious to hear your take: Are you seeing the same breakdown in traditional GTM mechanics? What’s your version of “SEAL Team Six” internally?

#marketing #sales #ai #gtm

Thanks for reading Playbook Broken! I’d be ridiculously grateful if you shared it.

Playbook Postscript

* This is season 1, episode 4 of Playbook Broken, a part of MarTech.org and republished here on my personal Substack. Portions of the post were created through Human-AI collaboration, and the episode was recorded in Vimeo and edited (by me, a human!) in Descript.

* I’m doing an experiment in storytelling on TikTok and LinkedIn, find me there and see what I’m up to. I’m having fun with it. 10,000 hours, right?

* Here are some book, TV and music recommendations:

* Book: The Children of Húrin is one of the three 'Great Tales' of the Elder Days from J.R.R. Tolkien's The Lord of the Rings universe. This book takes place in Middle-earth thousands of years before the events of The Hobbit and The Lord of the Rings, and was a ton of fun to read.

* Book: Do not sleep on reading Orbiting the Giant Hairball, which is not to be missed. It’s a joyful, frustrating, and important book for anyone seeking to live a creative professional life in a big corporation. I wrote about it on LinkedIn, but the algorithm didn’t love my post, and no one saw it. Here’s your chance.

* TV: The Gilded Age is deliciously ridiculous and fun. Carrie Coon reading a dictionary would interest me at this point.

* Music: I’m told the new Justin Bieber album is good but I haven’t tried it. Instead, I’m hooked on the 502s.

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