In September of 2025, I stood in front of 120+ landscaper owner-operators to talk about technology adoption. Me – the CTO who builds software for a living – teaching contractors about getting their crews to use apps. The irony wasn't lost on me. Halfway through my talk, as I watched

Two years ago, I stood on stage at our 0111 Conference and introduced the CTO Levels framework. We'd been doing hundreds of assessments by then, and the framework was working. CTOs were finally seeing the complexity of their role laid out in a way that made sense. They

When it comes to our technology—the thing our entire business is built on—we have this bizarre, almost dysfunctional relationship.

I asked a room full of CTOs to agree with something before they saw it. About 37% raised their hands. The rest stared at me like I'd just asked them to deploy to production on a Friday afternoon. Then I showed them the slide: The role of CTO

You know that feeling in your gut? The one that wakes you up at 3am wondering if you're building your tech organization all wrong? I stood in front of 200 founders at SaaS Academy in San Diego, and when I asked who had concerns about their dev team&