When should a Founder stop Selling and Hire a Salesperson?

When should a founder stop selling and hire a sales team? It’s a question I get all the time from early-stage founders, especially those who just landed seed or Series A.

Here’s my belief:

You don’t stop founder-led selling too early.

You do stop when you’ve hit repeatability.

Think of founder-led selling like cutting a trail through dense woods. At first, it’s slow, messy, and inefficient. But if you do it enough times, you start to see a path forming. You know which trees to avoid, where the loose rocks are, and how to explain your value so it lands. That’s the point when it’s time to bring in a sales team.

✅ You’ve found a real pain and a repeatable buyer.

✅ You’ve got messaging that consistently resonates.

✅ You’ve closed more than a handful of deals without pivoting your story every time.

✅ You’re no longer guessing who the buyer is or how long deals take.

Don’t hand off sales to someone else until you know what great looks like. Because if you don’t know, how will you train them? Manage them? Know if they’re any good?

I've worked with dozens of founders on this exact journey and every time we waited until the trail was worn in just enough, their first sales hire didn’t just survive, they scaled it.

So I’m curious, if you’re a founder, where are you on that trail? Still cutting it yourself? Or ready to bring others along for the climb?