← Jacob’s writing
Jun 10, 2026 · Lessons

We cut sales from five people to one. New revenue doubled.

We downsized our sales by 80%. New revenue doubled.

More salespeople doesn't always mean more pipeline. In a small market, it often means more noise.

Here's the thing about the sports market: you know exactly who your customers are. A finite number of programs, a finite number of coaches, a finite number of buying windows per year. And in a market that small, your customers likely already know about your product. More outreach doesn't change that. It just means the same coaches are hearing from you more.

After we raised money we hired. Three AEs, a manager, a BDR. The math felt obvious: more people, more pipeline, more closed deals. For 18 months the results didn't quite follow. I didn't understand what was happening until I got back in the seat myself.

The constraint was never bodies. It was conversion.

Budgets get set once a year. A coach who loves you in March can't do anything until August. A program that's genuinely interested today might not have a real conversation until after their season ends. You can have a full team generating activity and see nothing close for six months straight.

In the sports market, the question isn't whether you can reach enough people. You can reach all of them. The question is whether you can get the meeting in the first place, and then whether you can actually close it once you're in the room. That's a creativity problem. A relationships problem. A quality of interaction problem. A product problem.

When I understood that, the answer became obvious.

We downsized and put those resources into the things that actually moved the needle.
1. We hired engineers so the product could create more pipeline on its own.

2. We made sure the people carrying quota were the best at building relationships, demoing the product, and closing business.

3. And we stripped everything that wasn't direct sales activity off their plates. Automated the CRM. Took renewals out of their hands. Cleared the runway.

Our best people were now selling the best possible product, without broken systems slowing them down. It was freeing.

New ARR per sales rep went from $300K to $1.2M.

Seems obvious right? But it's anything but. When you are small and things are working, more people seems like the answer, but it rarely is.

We eventually grew the team again, because we realized travel built pipeline, and one person couldn't be everywhere. That was a real constraint. Worth hiring for.

Removing the fake bottlenecks made the real ones visible.