🏄🏼‍♂️ Scott Leese

I lost 25 of 30 salespeople in my first week.

The company had 6-8 months of runway left. The office was on 6th Street in Austin. I'd walk back from lunch and see reps literally at the bar with a pint and a shot of whiskey.

People showed up whenever they wanted, left whenever they wanted, went drinking at lunch. Total disaster.

So I got everyone together and laid down the law:

All this stuff is going to change. You're either with me, or you're not. You can quit right now, or I'm going to find you out in the next 72 hours and fire you.

After the first week, 25 of the 30 were gone. Either they left on their own because they didn't want to change, or I got rid of them.

The executive team freaked out. They thought I sabotaged them.

I said "you need to trust me. You brought me here for a reason."

Then I rebuilt three things.

- First, the culture. You can't sell if your team is drinking at the bar during work hours. That's ground zero.

- Second, how we sold. The old method was pure car sales. "Hey, this is what we do, it's on sale now for 50 bucks, if you buy today we'll drop it to 40." Fake urgency. Discount discount discount. No pain. No value. I had to reconstruct the entire selling method around understanding the buyer's actual problem.

- Third, the price. We were selling it for about 30 bucks a month. I raised it to 300. 10x! Everybody told me I was insane. I'd just fired all the salespeople and now I'm raising the price by 900%.

I got in the trenches with the five who stayed and started selling a few deals myself. They started figuring it out, and 𝘄𝗲 𝘁𝗼𝗼𝗸 𝘁𝗵𝗮𝘁 𝗰𝗼𝗺𝗽𝗮𝗻𝘆 𝗳𝗿𝗼𝗺 𝗮𝗯𝗼𝘂𝘁 𝘁𝗼 𝗿𝘂𝗻 𝗼𝘂𝘁 𝗼𝗳 𝗺𝗼𝗻𝗲𝘆 𝘁𝗼 𝗮 𝗻𝗶𝗻𝗲 𝗳𝗶𝗴𝘂𝗿𝗲 𝗲𝘅𝗶𝘁.

Those five who stuck with me all became sales Directors and VPs of Sales, or even a founder at their own company.

Sometimes you have to burn it down before you can build it up.

A founder paid a guy $200K to close zero deals.

Not a typo. Zero. Almost a full year as Head of Partnerships at an SMB company selling to real estate, and not one closed deal. The founder wanted to go up market before he'd nailed the direct motion. So he hired a corporate resume with an impressive title instead of somebody who could actually sell.

That's what happens when you confuse ex "brand name" with competence. And too many founders do it.

I know you want to escape selling. I know you see founder-led sales as a phase to rush through instead of what it actually is: the education that earns you the right to delegate. You can't teach somebody else to sell your product until you've at least tried to figure it out yourself. Understand the difficulty. Document what works. Hand off a playbook.

When you are ready to hire, here's one playbook.

Number one. Hire a sales leader who wants to do IC work, not "can also do" IC work. Somebody who finds it essential to sell it themselves and build the process at the same time. Not somebody who just looks the part.

Number two. Hire three AEs at once, not one or two. One will be great, one will be good, one will suck. You don't know which is which yet, and you can't figure it out with a sample size of one. When you only hire two, they buddy up and benchmark against each other. Nobody pushes. Add that third person and at least one doesn't care about being nice. The competition gets real.

Number three. Hire a RevOps lead next. Forcing a sales leader to build Salesforce dashboards is a waste of time and money. My inbox is littered with Founders and Sales Leaders telling me they realized too late how critical this was early on.

And the people who win those first seats aren't usually the ones with the most impressive resumes. They're the ones who love this work and this stage. The ones who take a ten-minute founder monologue and turn it into a fifteen-second pitch that makes the prospect say yeah, that's exactly what we need.

Sell until you can teach it. Then hire people who can actually do the work.