The CAIO Paradox
I never created a Chief AI Officer role on my team. Here's what I did instead — and why the title was never the point.
Every few weeks another company announces its first Chief AI Officer. The press release is always the same shape: a new executive, a mandate to "lead AI strategy," a slide about transformation. The company that made the hire feels like it did something. Often, it just bought itself six more months before anyone asks the question that actually mattered.
I never created that role on my team. I don't think I should have.
The paradox
Here's the problem with a dedicated AI executive: the moment you create the role, you've also created a bottleneck. Every AI decision now has an owner, which sounds like progress until you notice what it actually does — it gives everyone else in the organization permission to stop asking the question themselves. Product managers stop wondering if a feature should be AI-native, because that's the CAIO's job now. Engineers wait for the AI roadmap instead of building the AI-native version of what they were already shipping.
The question that used to belong to everyone now belongs to one person, and that person hasn't onboarded yet.
Meanwhile, the competitor who never made the hire is asking the question in every product review that was already on the calendar.
What I did instead
I run the product portfolio reviews across our product line. I didn't wait for a mandate to change what those reviews ask. I just changed the first question.
Instead of "what are we building next," it's "where does this become AI-native before we build it the old way." Same meeting, same people, same calendar — different default. No new title, no new org chart box, no six-month search.
This maps directly onto a framework I keep coming back to: PLANT, BUILD, HARVEST. PLANT is the cheapest phase — it costs nothing but a different question asked in a meeting that already exists. BUILD is where the capability actually gets created, team by team, feature by feature. HARVEST is the phase everyone wants to skip to, the EBITDA-moving part — and it only shows up if the first two phases actually happened.
A Chief AI Officer hire tries to start at HARVEST. It skips PLANT entirely, because by the time the org has agreed it needs a dedicated AI executive, nobody in the building has spent months quietly asking the cheap question in the rooms where it costs nothing to ask.
The leaner stack, applied to roles
I think about this the same way I think about the Leaner Stack Paradox — the idea that smaller companies have a structural AI advantage because they have fewer layers between a decision and its execution. A dedicated AI executive is a layer. It sits between the question and the person who could just ask it.
A mid-market company doesn't need to be huge to make this trade. That's the advantage, not the excuse. I don't need to wait for a CAIO to greenlight asking whether a feature should be AI-native — I run the review where that question lives. Every operator running product, ops, or growth at a company this size has the same option: skip the hire, keep the question, ask it yourself in the meeting you already run.
The organizations that end up AI-first won't be the ones with the best org chart. They'll be the ones where someone with real product authority decided the question was worth asking before anyone gave them a title for it.
If this was useful — more like it, every two weeks.
AI, building, and owning — biweekly, for operators who ship.