Fractional AI / CTO Advisory

AI strategy and execution for companies betting on what comes next.

I serve health-tech and wellness operators, plus any company adopting, examining, building with, or investing in AI. Quiet confidence over hype. Shipped work over slideware.

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Glowing amber neural network filaments weaving through a dark lattice

Who I work with

Operators, executives, and investors moving on AI.

Health-tech and wellness operators

EMR-aware, HIPAA-conscious work across AWS and HubSpot stacks. Translate clinical and operational workflows into shipped AI features.

Executives adopting AI internally

CEOs and CTOs who need a calm, technical partner to examine vendors, pilots, and the build versus buy calls without the hype.

Investors evaluating AI bets

Diligence on AI companies and infrastructure plays. Architecture, moat, cost curve, and team realism, in plain language.

What you get

The work of a fractional AI/CTO.

Six places I add the most leverage. Not every engagement touches all six. Most touch three.

AI roadmap and prioritization

From scattered ideas to a sequenced plan tied to revenue, risk, and the team you actually have.

Architecture and stack review

Data, model, vendor, latency, and cost. RAG, agents, and workflow automation evaluated against your real constraints.

Pilot to production

Move beyond demos. Reliability, evaluation, observability, and the unglamorous plumbing that makes AI ship.

Team enablement and hiring

Org design for AI. What to hire, what to upskill, what to outsource. Coaching for engineering leaders.

Investment diligence

Technical and operational diligence on AI companies. Honest reads on defensibility and execution risk.

Governance, security, compliance

AI policy, data handling, model risk, and audit posture that holds up in regulated and enterprise contexts.

How engagements work

Start small. Scale to fit.

Most companies engage me somewhere between idea and pilot. The work compounds from there.

01
Discovery call
A focused conversation. Where you are, where you want to be, and whether this is the right fit.
02
Scoped diagnostic
A short engagement to map the terrain. Architecture, team, vendors, risks, and the highest-leverage moves.
03
Ongoing advisory or sprint
Fractional retainer for continuous leadership, or a fixed-scope sprint to ship a specific outcome.

Engagements

Four ways to work together.

Most engagements start with a Readiness Diagnostic or a discovery call. Scope and investment are quoted per engagement after a short conversation.

AI Readiness Diagnostic

A short, decisive engagement to map the terrain before you commit capital.

2 to 4 weeks. Fixed scope.

Best for. Operators and executives who need a clear-eyed read on where AI fits, what to build versus buy, and what to do first.

Architecture, data, and vendor review
Use-case shortlist tied to revenue and risk
Team and hiring gap analysis
Written report and executive readout

Request the diagnostic

Fractional CTO Retainer

Most common

Ongoing technical leadership without the full-time hire.

Monthly retainer. Typically 3 to 6 months minimum.

Best for. Founders and CEOs who need a steady technical partner in the room for roadmap, hiring, vendor calls, and the hard decisions.

Weekly leadership cadence with the founder or CEO
Roadmap, architecture, and hiring guidance
Vendor and contract review
On-call for board prep and key technical conversations

Discuss a retainer

AI Build Sprint

A fixed-scope sprint to move one AI initiative from idea to shipped.

4 to 8 weeks. Outcome-based.

Best for. Teams who know what they want to ship and need senior leadership to sequence the work, set the evaluation bar, and stay close to delivery.

Defined target outcome and success metric
Architecture and evaluation plan
Hands-on technical guidance with your team
Reliability, observability, and handoff

Scope a sprint

Investor Diligence Report

Independent technical and operational diligence on an AI company or investment.

1 to 3 weeks. Fixed scope.

Best for. Funds, family offices, and acquirers evaluating an AI bet who want an honest read on defensibility, execution risk, and cost curve.

Architecture, model, and data review
Team and execution assessment
Moat, cost, and competitive read
Written report and partner-level debrief

Request a diligence engagement

Background

A technologist, athlete, and leader.

CTO experience in health-tech infrastructure. Air Force veteran. Elite OCR athlete. Author of the Seven Gates framework for leadership maturation. The same discipline that builds platforms builds people.

Full background About Ken