Most first-time CEOs hire who they like. The job is to hire who they need. A retrospective on the moment my company started compounding.

We doubled EBITDA from 10% to over 20% in three years. The work was not financial. It was the decision to say no to a hundred things that did not earn their oxygen.

Twenty years of design craft did not prepare me for the CEO seat. They prepared me for the seat I had to leave behind.

I am not a doctor. I want to say that at the start, not as a legal disclaimer, but as context for why what happened next surprised me.

I have spent 25 years making decisions inside large organizations — reading data, mapping dependencies, catching the thing nobody mentioned in the meeting that would break everything six weeks later. I thought I was reasonably good at holding complexity in my head.

Then I gave an AI my actual health data and asked it to audit my supplement stack. What came back made me rethink what I understood about the technology — and about where the real opportunity in AI is going to be found.

A POV piece. Not a retrospective. Written May 9, 2026, the week I applied for a job that may or may not be mine, in a category nobody has cracked yet.

For thirty years, retailers have called their loyalty work "programs." That word is the problem. That model is dead, even if its budget is still funded.

I was in a conference room at Nike's World Headquarters in Beaverton, presenting the latest iteration of our commerce platform. The interface work was clean. We'd spent months on information architecture, user flows, behavioral models. The work was good.

For the first decade of my career, I owned nothing. No P&L. No headcount budget. No final say. But I learned how to move things anyway.

Before growth teams, before funnels, before A/B testing at scale—there was just watching how people actually used the thing you built.

Between 2000 and 2006, most digital commerce initiatives died. The ones that survived shared patterns I didn't recognize until years later.