Fractional Chief AI Officer
I led Microsoft's Copilot for Business launch. Now I'm the CAIO for five companies at once.
Fractional Chief AI Officer for companies that can't wait.
The Role
What a Fractional CAIO actually does.
Not services. Not a SOW menu. This is the honest job description — what I'm hired to own, week over week, across the companies I work with.
AI strategy & roadmap
Board and exec-level positioning: what to invest in, what to ignore, what moves the P&L.
Use-case identification
Prioritizing the AI opportunities that actually fit your business — not the ones trending on LinkedIn.
Build-vs-buy evaluation
Cutting through vendor noise across your stack, so you're not stitching together shelfware.
Agent & workflow deployment
Shipping AI into your operations — not decks, not pilots, actual production workflows.
Team & exec enablement
Getting your senior team literate and confident — so AI decisions don't bottleneck at one person.
Ongoing oversight
Fractional, not a one-off audit. I stay on the bench as AI and your business evolve.
Build Log
What I'm building this week.
Wiring a Vapi voice agent into the Readiness Audit
First take of the audit voice loop. Vapi + OpenAI + a scoring rubric. Lots of rough edges — shipping anyway.
Five companies, one inbox — my CAIO ops stack
Walkthrough of how I run CAIO work across five companies from a single AwareOS pane. Still iterating on the context-switching UX.
An AI agent that writes my Friday partner notes
40 minutes of work saved every Friday. Built with Claude + a Notion DB + one cron. Sharing the prompt.
The Arc
Thirty years. One throughline.
I joined Microsoft in 1996. I co-founded Aware Group in 2016 and exited to HSO in 2024. I led the launch of Copilot for Business, and now I run AwareOS and serve as CAIO across five companies. The throughline: turning emerging technology into real business value, before the rest of the market catches up.
The Audit
In 10 minutes, I'll tell you where your business actually stands on AI.
Not a PDF. Not a quiz. A conversational AI that asks you 8–12 questions tuned to your business, and produces a tailored readiness report on the spot.
Take it in the car. Take it on the phone. Take it with your CFO in the room.
Jay's AI Readiness Audit
Hi, I'm Jay's audit assistant. Ready when you are.
Thinking
What I'm writing about.
What I Learned Launching Copilot That Most AI Consultants Miss
The gap between demo-day AI and real enterprise adoption — and what it takes to close it.
Read essayThe 5-Company View: Patterns I See as a CAIO
What working across five portfolios concurrently reveals about where AI actually lands.
Read essayWhen to Hire a CAIO vs a Fractional vs a Consultancy
A decision framework for founders who know they need AI leadership but don't know what kind.
Read essayWho This Is For
Who I work with.
The altitude filter, up front.
I work with
- Founders and CEOs of $5–100M businesses navigating AI transformation
- Boards and exec teams who need senior AI leadership without a full-time hire
- Fractional CMOs, CFOs, COOs, and CTOs who bring me in as the AI counterpart on their client accounts
I don't work with
Very small businesses, DIY AI builders, or anyone expecting a one-off audit and done. If that's you — I'd love to point you somewhere useful.