Most Mid-Market CEOs Are Solving the Wrong Sales Problem

ChatGPT Image Mar 12, 2026, 11_55_34 AM

I’ve had some version of the same conversation about 150 times in the last twenty years.

CEO calls. Revenue isn’t where it needs to be. Pipeline looks fine on paper but deals keep slipping. Top rep is carrying the team while everyone else is mediocre. And the CEO is stuck in the middle of it. Stepping into deals at the last minute. Not trusting the forecast. Can’t step away without something falling apart.

They all say the same thing when we first talk.

“We have a closing problem.”

They don’t.

After two decades of working inside these organizations, here’s what I know. Every sales problem comes down to one of four things.

Talent. You have the wrong people. They work hard. They might be good cultural fits. But they don’t have the DNA for sales and no amount of training will change that.

Infrastructure. You don’t have a real system. You have a collection of people doing sales-like activities and hoping things close. No defined process. No real pipeline standards. No playbooks. Just activity and optimism.

Skills. Your people can’t execute the conversations that win deals. They’re good at presenting. They’re good at relationships. But they can’t build a compelling case, handle real resistance, or get a prospect to a decision.

Leadership. Nobody is actually leading the sales organization. It’s being managed from a distance. Report reviews. Pipeline meetings where nothing changes. Someone waiting for someone else to figure it out.

One of these four is your constraint. Maybe more than one.

Most sales advice tells you what to do without helping you figure out which problem you actually have. So you end up hiring when you need to train. Or training when you need to fire someone. Or buying software when what’s broken is the person running the team.

You can’t fix the right thing until you know what’s broken.

That’s the book I’ve been working on since last fall. I didn’t want to write another sales book. There are plenty of those. I wanted to write something that actually helps you find the problem first. And then gives you what you need to fix it.

It’s called:

The Four Pillars of Your Sales Engine.

It walks you through the symptoms. The pipeline that’s misleading you. The role you’re stuck playing in your own organization. The conversion math you’re probably missing. By the time you finish Part 1, you’ll recognize which pillar is cracked.

Then it shows you what each broken pillar actually looks like. And what to do about it.

Click here to grab it 

If you read it and recognize your company in those pages, reach out. That’s what it’s for.

Adam

Adam Boyd