The Fractional CAIO
You’re investing in AI — $500k–$3M a year in engineering — and nothing is shipping that moves revenue or cuts cost. That’s a fixable problem.
I run AI transformation programs for PE-backed SaaS and fintech companies valued above $1B. The outcome: product changes that move metrics, engineering spend that returns instead of burning, and a team that can run and extend AI without me after 12 months.
The goal of every engagement is my own redundancy. I work through your team, not over them — on your existing stack, with no vendor lock-in, no outsourcing, no AI theatre.
You're spending on AI. Nothing is shipping.
The AI people often felt frustrated because the product team didn't know what AI could achieve, and the ML engineers didn't always understand the product needs.
What we were really missing was someone with experience in building and leading an AI team.
What you get
Revenue and cost that move
AI products ship and change metrics — conversion, ARPU, retention, support deflection. Not experiments that sit in staging.
Engineering spend that returns
$500k–$3M/year in AI engineering stops burning on misdirected bets. Direction is validated before the sprint starts.
A team that runs it without me
By month twelve, your team can run and extend AI without external dependency — a higher exit multiple for the fund, and no ongoing consulting cost.
Why partner up?
Technical depth
27,000 hours of expertise (recommenders, NLP, CV, RL). That means I engage credibly from CEO conversation to VLLM config — without a team of consultants behind me.
The trifecta no other advisor has
Top AI lab background (DeepMind) + shipped to billions + full altitude range from board strategy to engineering detail. Each attribute exists individually in other advisors. The combination doesn’t.
Organizational fluency
Most AI failures aren’t technical — they’re organizational. Getting real information out of teams that communicate indirectly, building trust in hierarchical structures, getting honest assessments from people who won’t say it straight: these are learned skills. They change the quality of the diagnosis.
How it works
Strategy firms leave after the deck. Software houses build it and own the dependency. I stay through the change — until your team can run it without me.
| The Fractional CAIO | Strategy firm | AI software house | Full-time hire | |
|---|---|---|---|---|
| What you get | Shipped product, trained team, capability that persists | Slide deck and a plan | Built product — ongoing dependency | A person who needs direction you don't yet have |
| After engagement | Your team runs it without me | You have a roadmap | You have a product you can't extend | 6–12 months to get up to speed |
| Talent development | Core focus — build and coach your AI team | Rare | None — they own the capability | Self-directed — needs leadership |
| Vendor dependency | None — works on your existing stack | May push proprietary tools | High — architecture tied to their team | None |
Trusted by leaders
"Jack brought a structured approach to prioritizing AI projects. His energy, clarity, and directness helped us shift focus to higher-impact areas, make better use of existing resources, and adopt a hypothesis-driven process."
"Jack's consulting helped us understand how the portfolio company approached AI — how it's built, how it operates, and where they need to adjust. His ability to explain complex ideas and influence the team made a real difference."