Your sales leader should teach you sales.

A client had a VP of sales who cost them nothing.

I mean literally nothing. No salary. He was 100% commission. An early friend of the founder who’d helped get the company off the ground.

On paper, a great deal. But it was one of the most expensive roles in the company.

Here’s what I heard when I interviewed the team:

• He didn’t track his dealflow or any numbers, so nobody knew what was working.
• He was still running the outreach playbook from years ago, when it worked.
• Feedback didn’t land. He got defensive, and he was a friend, which made it harder.
• As a result of all of this, the founder and COO kept getting pulled back into sales.

The founder’s plan was to become a pro partnerships person themselves, so they could coach their friend into the role.

I pushed back on that. At this stage of a company, your sales leader should be teaching you sales, not the other way around.

You need someone who shows up with a playbook, measures everything, and brings in new tactics before the old ones stop working.

That doesn’t mean the friend has to go. He was well liked and great for the culture. But he couldn’t run the department anymore. The options were either an honest conversation about his role and a reset on expectations, or bringing in an experienced rep to lead.

These are some of the hardest decisions founders make, because every company has people who helped build the company but aren’t an ideal fit anymore.

But as your company changes, the people often need to change, too. Sometimes they’ll change proactively, sometimes willingly, or sometimes not at all.

But the longer we prolong that reality that things have to change, the more it hurts us.