Selling to the C-suite is for losers

When I pitched venture investors about AI pricing software a decade ago, many were excited that it was a C-suite sale. CEOs and other leaders hardly care about most things that go on in a business–they’re spread peanut butter thin. If they care usually it’s because it’s a fire that has to be put out. So to be a strategic vendor that captures their interest and imagination can seem like a huge advantage–big budgets, top-down procurement.

But it isn’t an advantage. It’s a curse.

It’s far better to have a product that appeals to a more junior user. That’s part of the furniture. Yes, the C-suite has budget. But being part of the day to day has its advantages. How many of the hypergrowth AI startups sell to the C-suite?

And before I get to it, I know lots of our readers are account execs who pay the bills by selling to the C-suite. This post is about early stage startup strategy, not knocking enterprise sales. Of course, I’ll put some stuff in here for you to go tell your product team you need to help close new deals and retain existing ones.

How we got to $10mm in 13 months

Before AI was a thing, I joined Drawbridge when it was a mathematical proof on a scrap of paper. There was some synthetic data (a fancy way of saying “we made it up”) to prove it worked. But zero actual real world proof. We figured that out, and started selling. Our first customer check was $10k. Our second, about a week later, was $150k.

I’d like to say it was off to the races from there. Instead we spent 3 months in the pits putting an engine in the car, mounting the tires, and maybe also building a suspension before it was roadworthy. Just keeping it real–it’s never easy.

But we had that velocity because the CEO was left out of it. We did things with data that a smart person could ask hard questions about. We were brand new and, at the time, doing absolutely zero volume. Our first $250k in agreements was closed before we ever served a single ad. None of this would have stood up to C-suite scrutiny. But we weren’t selling to the C-suite–we were selling to the most junior person on the team.

The best sales motions have 3 things in common

The best sales motions sell to a single stakeholder with the pain, budget, and authority. Typically because they have the pain they are also your user. How has Cursor grown so quickly? Because every engineer hates writing rote code (ie has the pain), and also has budget and authority to pay $20/mo for vastly greater efficiency. They are the one using the product so they can do the trial and put in their credit card. No committee required, no feathers ruffled, no politics. 

Seems obvious because it is. But is that how you sell?