If we had to bet on the one hire most likely to make or break a startup between Seed and Series B, it’s the Head of Sales. Yet this is the same hire startup founders are most likely to get wrong. 

It’s understandable. The stakes are high. You’ve got a product with some traction, a few logos on the board, and a hunch that if you could just clone yourself, you’d finally unlock repeatable growth. So you go out and hire someone with an impressive resume: a VP from Stripe, or an AE from a hot growth-stage startup, someone who sold $2M in ARR last year with a top-tier logo sheet to match. But a few months in, something feels off. The demos keep coming, but the deals aren’t closing. Pipeline is thin, and your new Head of Sales is badgering you for BDRs, RevOps, and enablement infrastructure you simply don’t have. 

Suddenly, you realize you haven’t hired a builder. You’ve hired a driver accustomed to Formula One conditions, while you're still busy laying asphalt.

There’s a fundamental misunderstanding many founders have about this role in the early days: the belief that sales is a function you hire to scale, when in reality it’s one you hire to create. Until your startup has a rinse-and-repeat sales motion (a clear ICP, predictable conversion, and objection handling that works), you’re not scaling anything. You’re still in discovery mode. And the person you need isn’t an operator who can manage a team of ten. It’s a founder-type who also happens to sell.

The best early sales leaders aren’t closers, they’re architects. They don’t just sell, they build the playbook for how to sell. They write the first cold emails, run the first outbound sequences, tweak the first decks. They know how to hunt, not just farm. They iterate. They’re comfortable hearing no. They’re allergic to excuses and immune to resource envy. They thrive in ambiguity. 

We’ve seen too many great products stall because the wrong sales hire burned a critical year and cash runway. Founders need to approach this hire with the same care and scrutiny they’d use for a co-founder, or a significant other. Because in many ways, that’s what this person becomes: a partner in figuring out how to turn your product into a business.

Don’t get blinded by brand names or upmarket pedigree. Don’t outsource judgment. Look for builders, not scalers. Remember that the scope of this hire goes far beyond designing decks, outbound sequences, and cold email messaging. It also requires a maniacal focus on customer feedback, a nose for sniffing out the ICP, curiosity about the competitive landscape and avenues of differentiation, and a willingness to iterate endlessly. Above all, find someone who is as hungry as you are to prove this thing works, one deal at a time.