When to Hire Your First Sales Leader

Founders often ask, “When should I hire a Head of Sales?” The real question is: what problem are you trying to solve?

If you're still figuring out who your customer is and what messaging works, you're not ready. A great sales leader isn't there to find product-market fit — they're there to scale what’s already working.

Once you have 2–3 reps consistently hitting quota, deals closing without founder involvement, and a repeatable sales process — that’s your signal. A sales leader can now bring structure, coach the team, and help you scale without losing quality.

Hiring too early can create misalignment. Leaders need something to lead. Without proof points and momentum, they’ll end up doing founder-level selling in a role that doesn’t match their strengths — and nobody wins.

So ask yourself: do I need more selling or more scaling? If it’s scaling, it might be time. If not, keep building — and bring in your sales leader when the engine’s ready to run faster.