When founder-led sales becomes the bottleneck.

The pattern is so common it’s almost a stage of growth: the founder closes the first 50 deals, the board starts asking “when are we hiring a VP Sales,” and six months later there’s a $400K hire who can’t seem to gain traction. The diagnosis “we hired the wrong person” is usually wrong. The transition itself is the hard part — and the company was rarely ready for it.

Three signals you’re ready

1. You can repeat your own wins on paper. If you, the founder, can describe in writing why deals close — and another human can use that document to take a meeting and not freeze — you have a sales motion. If you can’t, you don’t.
2. Pricing is no longer a per-deal negotiation. When you’ve shipped a price book and the last ten deals closed within ±15% of it, the motion is repeatable enough to hand off.
3. Your pipeline doesn’t crater when you take a week off. This is the cleanest test, and almost no founder-led companies pass it.

If two of three are true, you’re ready. If only one is, hiring a VP Sales will make things worse, not better.

The transition design

The bridge role is not “VP Sales.” It’s a player-coach: someone who closes deals next to you for two quarters and quietly builds the playbook, the comp plan, and the first two reps. Then they become VP Sales — or hire one over themselves.

This is unsexy, slow, and a tenth the cost of getting it wrong the other way.