The job

What a fractional CAIO actually does.

  1. Decide where AI belongs β€” and where it doesn't.

    A workflow-by-workflow map of your operation, ranked by payoff and risk.

  2. Build the agent teams.

    Design, deploy, and tune coordinated agents for the work that eats your team's week.

  3. Own security and compliance.

    Data boundaries, local deployment where required, approval gates everywhere.

  4. Train the humans.

    Your team learns to direct agents, review their work, and know when to step in.

  5. Report to you.

    Monthly: what's running, what it's producing, what's next.

  6. Earn it monthly.

    Month to month. Stephen would rather be re-hired every month than locked in.

Who this is for

Founders with a team that's stretched.

Not a fit

  • X

    Businesses still building their first process

  • X

    Anyone who wants a chatbot and a press release

  • X

    E-commerce and D2C brands

  • X

    Teams looking for a vendor instead of an executive

Best fit

  • βœ“

    Founders and CEOs of service businesses at seven figures and up

  • βœ“

    Processes in place and a team that's stretched

  • βœ“

    Law, medical and health, coaching and consulting, professional services

  • βœ“

    Regulated industries are welcome β€” that's the specialty

The first 90 days

Assess. Pilot. Scale.

One workflow at a time, with a number attached. Nothing scales until the last thing proved out.

  1. Days 1–30 Β· Assess

    Workflow mapping, data and security review, first-pilot selection. Deliverable: the roadmap, with the first pilot scoped and a target number attached.

  2. Days 31–60 Β· Pilot

    First agent team live on one workflow. Measured weekly. Approval gates in place from day one.

  3. Days 61–90 Β· Scale

    Second and third workflows. Team training. Governance set so the business can run the agents without Stephen in every meeting.

  4. After 90 Β· Cadence

    Monthly executive report, weekly working session. New workflows added when the last one has proven out β€” not before.

How the engagement runs

Part-time. Defined cadence. No junior handoff.

A weekly working session and a monthly executive report. Month to month. Stephen does the technical work with support from the Automation Warrior team β€” you don't get handed to a junior.

The assessment is a fixed fee. The retainer is scoped from it, based on the number of workflows and the deployment model β€” cloud or private.

Frequently Asked Questions

Bring the workflow. Leave with a plan.

Thirty minutes. Stephen will tell you whether AI belongs there, what it would take, and what it would be worth. No deck. No pitch.