The First AI-Assisted Close

The operating model matters more than the model

Jason M. Lemkin 🦄 was my first CEO. He taught me that the best sales leaders don’t wait for permission to change how their teams operate.

Few months back Jason went public about replacing most of his sales team with AI agents. Bold move. Right instinct. But he runs a lean team by design.

I wanted to know if it could work inside a complex, scaled organization with real compliance requirements, cross-functional dependencies, and millions of merchants counting on us to get it right.

This week, we got our answer. An AI-assisted sales workflow (agentforce) moved a merchant through our pipeline from first touch to close. Not a pilot. Production.

It took months. It took conviction from people across the organization who chose to lean in instead of wait. I’m grateful for every one of them.

Here’s what I know now: the gap in sales isn’t between companies that have AI and companies that don’t. It’s between leaders willing to build the operating model for it and leaders still asking for a deck.

We’re #building.