July 27, 2026 · Go-to-Market

Most GTM problems are leadership clarity problems

The company that can't generate pipeline usually can't articulate who its best customer is. A pattern from dozens of CEO conversations.

Most GTM problems I see aren’t marketing problems. They’re leadership clarity problems.

After sitting across the table from dozens of CEOs and their teams — as an operator, a board member, investor, and an advisor — the pattern is remarkably consistent.

The company that “can’t generate pipeline” usually can’t articulate who its best customer is. The company “struggling with sales execution” usually has a CEO holding three conflicting definitions of the ICP — one in the deck, one in the CRM, one in their head. The company that “needs a better VP of Sales” often needs the founder to finish the GTM handoff they started two years ago.

Here’s what I’ve learned: you can’t fix any of this by handing over a playbook. I’ve tried. The playbook gets nodded at and shelved.

What works is a conversation:

  • Walk me through your last five wins. What did those buyers have in common?
  • If you lost your top rep tomorrow, what walks out the door with them?
  • What are you personally still doing in the sales process — and why?

That’s true for GTM. It’s true for almost everything else that lands on a CEO’s desk.

When you got GTM right, what actually unlocked it?

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