When to Hire Your First Sales Leader

The most expensive mistake in early GTM

Hiring a sales leader before you have a repeatable motion is one of the most common—and costly—mistakes enterprise technology companies make.

It feels right. You have traction. Investors are pushing. The board wants to see a "real" sales org. But here's what actually happens: you hire someone great, give them 6 months to ramp, and then spend another 12 months figuring out why the motion isn't working.

The problem wasn't the hire. It was the timing.

Signs you're not ready

• Founder-led sales is still working — If deals only close when the founder is in the room, you don't have a transferable motion yet.

• ICP is still fuzzy — If you can't clearly articulate who your best customers are and why, a sales leader will spray and pray.

• Deal size varies wildly — Inconsistent deal sizes signal you haven't found your repeatable wedge.

• Sales cycle is unpredictable — If you can't forecast when deals will close, you're not ready to scale.

Signs you're ready

• You've closed 5-10 similar deals — Pattern recognition is emerging.

• You can describe the buying process — You know who's involved, what they care about, and what triggers urgency.

• Non-founders can articulate the value — The pitch works without founder magic.

• You're turning down bad-fit deals — Constraint is a sign of clarity.

The middle path

Before the full-time hire, consider a focused GTM advisory engagement. Validate the motion, define the ICP boundaries, and build the playbook. Then hire someone to run it—not figure it out.

The goal isn't to delay growth. It's to make sure growth compounds instead of corrects.