Your VP Sales Can’t Save You: AI GTM in the Post-Playbook Era

Notes from the field ✍️When the product evolves faster than the buyer, the real advantage is learning how to sell what no one knows how to buy.

AI startups aren’t just reinventing technology. They’re reinventing go-to-market - mostly because the old one doesn’t work anymore.

The classic enterprise sales playbook - prove PMF, hit some revenue milestone, hire the big-name VP of Sales who brings their well-worn playbook - turns out to be less of a blueprint and more of a museum artifact in AI.

That playbook made sense when the buyer was predictable, the competition was clear, and the product didn’t change every quarter.

But in AI, the buyer is overwhelmed, the competition changes every month. And the product? Let’s be honest: half the time you’re still building it while you’re selling it.

Naturally, this creates some tension. Startups bring in a “name brand” sales leader - the kind of person who crushed it in classic SaaS - and what do they do? They apply the familiar motions: long sales cycles, land-and-expand, consensus building, the occasional round of golf. Except the customer doesn’t want a round of golf. They want to know how your model works, whether it hallucinates, how it’ll fit into their stack, and whether it’s going to break production at 2 a.m.

And so these companies stall. Because the old playbook doesn’t tell you how to sell a thing that even you don’t fully understand yet, to a customer who isn’t sure they’re ready to buy it.

So what is working? Two patterns I see again and again:

• High-horsepower generalists as leaders. Hungry, adaptable, curious, fast learners. The people who don’t say, “This is how we did it at [BigCo],” because, frankly, nobody’s done this before.

• Technical sellers as the team. The real edge in AI GTM? Technical sellers. The folks who can explain how it works, why it works, and when it might fail - and who buyers trust because they aren’t just selling, they’re guiding. Technical depth and cultural fluency are today’s GTM superpowers.

⚠ Caveat: This isn’t a dunk on experience. Experience is invaluable - when it evolves with the market. What fails is treating experience like a universal hammer, when the shape of the problem has changed. The seasoned VP Sales can absolutely be the high-horsepower generalist you need - but you have to look for signs they’re still playing the current game, not just replaying old wins. It’s not a default setting.

We’re all watching this GTM playbook get written - and rewritten - in real time. The question isn’t “Who can sell this?” It’s “Who can figure out how to sell this, while we’re all still figuring out what we’re actually selling?”