When do you genuinely need the CAIO?
Multiple departments with competing AI priorities; compliance or board pressure demanding formal governance; vendor contracts big enough to need an executive negotiating them; or an internal team that will execute if someone senior points. If two or more of those are true, hire the executive — and we'll say exactly that on a call rather than sell you coaching.
When is the coach the right first money?
You are the bottleneck and the decision-maker; there's no team to receive a "roadmap"; and what you need is one working system this month, not a transformation program this year. Start with one agent you own. If the business later outgrows that, you'll walk into the CAIO conversation already knowing how agents work — which changes what you buy and what you pay.
The trap to avoid either way
Anyone — coach, CAIO, or agency — whose model requires you to run on their platform, with their keys, has built their retention into your switching costs. Whatever you hire, make ownership a written deliverable. Ours is published.