The Danger of Defensive Honesty

by TheCROJo | Jun 29, 2026 | Founders, Leadership, Marketing, Migrate, Product-Market Fit, Revenue, sales

She had one week until the sales kickoff. New platform. Big launch. Skeptical team. She was rehearsing her answer to the question she knew was coming: “Does it actually work?” Here’s what she had: “It’s a first-gen product. There will be...

Shooting Myself in the Foot

by Zoya Wasti | Jun 17, 2026 | Founders, GenAI, Leadership, Migrate

In retrospect, I kept shooting myself in the foot. Not because I lacked talent or drive or the ability to figure things out. I had plenty of all three. But through every major career transition, every high-stakes decision, every moment when the pressure was highest...

The Talent Trap: Why AI Rollouts Are Really About Clarity

by TheCROJo | May 20, 2026 | Customer Success, GenAI, Leadership, Migrate, Revenue, sales

A senior marketing leader told me something recently that I haven’t stopped thinking about. His team was a few weeks into a major AI rollout. Enthusiasm was high. A small cohort of internal champions had been trained. Core work processes were being reimagined....

Stop Making Hard Things Harder

by TheCROJo | Apr 7, 2026 | Leadership, Migrate

When I was diagnosed with cancer, I had a choice. Say nothing and power through. Or tell people — not what was happening to me, but what I needed from them. I chose the second one. And the response surprised me. Not because people were kind. I expected that. What...

The Alluring and Breakthrough Mystery of “That Rep”

by TheCROJo | May 20, 2025 | Founders, GenAI, Revenue, sales

At every company I’ve worked with, there’s always “That Rep.” You know the one. Their calendar is packed with meetings that actually close. They consistently crush quota and live in accelerators. When competitive curveballs come their way, they...