Air Force Ken

Technology and AI officer · On demand

Your technology and AI officer, on demand.

You do not need a full-time technology officer. You need the right call at the right moment, from someone with no budget to defend and no vendor to favor. Already have a CTO or CDAO? This is the outside view they cannot give you.

Glowing amber neural network filaments weaving through a dark lattice

The record

Judgment built where it had to hold.

Walk the full résumé
24 hrs → 1 sec
Crisis battle damage assessment, after he commissioned three AI programs
20×
Targeting speed from the IC data analytics he mapped for Air Combat Command
#1 of 37
Joint-service majors and lieutenant colonels, National Reconnaissance Office
$1.5B+
Permanent funding unlocked by his 34-million-datapoint study
1,000+
Venture offerings diligenced for In-Q-Tel, DIU, and NeedipeDIA
$500M
Advanced-technology contracts driven as a Defense Venture Capital Fellow

USAF Lt Col (ret). Air Force Lead on the White House AI Futures Working Group. Deputy Chief at the Defense Intelligence Agency. Chief Data and AI Officer and CTO for operating companies since 2024.

Why an outside officer

Most companies need the judgment. Few need the full-time hire.

On demand, by design.

A full-time technology officer is a large fixed cost for a job that comes in bursts: a vendor decision, a hire, a build, a crisis. Bring in senior judgment when the decision is live, and stop paying when it is made.

Impartial, even when you have a CTO.

An inside officer has a budget, a team, and past decisions to defend. I have none of those and no vendor to favor. Good leaders with strong CTOs and CDAOs still want one voice in the room with nothing to protect.

Across national security, health tech, and consumer.

What one field solved years ago is often what another is stuck on today. I bring the pattern from the field that already solved it.

What you get out of it

  • A straight, impartial answer on the decision in front of you
  • AI on the work that repeats, added safely: shadow, compare, cut over, roll back
  • Fewer tools, lower spend, faster decisions
  • A team that can run it without me

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 an on-demand technology and AI officer.

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.

01IDEAUse case. Risk.02ARCHITECTUREData. Model. Vendor.03PILOTEval. Metric.04PRODUCTIONReliability. Cost.05OPERATEObservability.STARTSTEADY STATE
  1. 01

    Discovery call

    A focused conversation. Where you are, where you want to be, and whether this is the right fit.

  2. 02

    Scoped diagnostic

    A short engagement to map the terrain. Architecture, team, vendors, risks, and the highest-leverage moves.

  3. 03

    Ongoing advisory or sprint

    An on-demand retainer for continuous leadership, or a fixed-scope sprint to ship a specific outcome.

Done for you

Audit first. Then fix. Then keep it running.

Three steps, each with a fixed scope. You can stop after any of them and keep everything you paid for.

Step 01

AI Readiness Audit

I look inside the business and hand back a ranked list of what to fix first.

Fixed fee, quoted in writing

Confirmed after a short scoping call. No open-ended hours.

5 business days. Fixed scope.

  • Read-only review of your tools, workflows, and handoffs
  • A baseline: hours, cost, and error rate on the work that repeats
  • Fixes ranked by payoff, risk, and effort
  • A written plan and a one-hour readout with you
Step 02

Turnaround Sprint

I deploy the top fixes. You see what changed by the end of the sprint.

Fixed fee, quoted in writing

Confirmed after a short scoping call. No open-ended hours.

2 weeks. Fixed scope, agreed before work starts.

  • Each automation runs in shadow mode beside your current process first
  • Side-by-side results you can check before anything is switched on
  • Cutover one workflow at a time, with your sign-off
  • A rollback path for every change, and a handoff your team can run
Step 03

Run and Grow

I keep the agents running, measure them, and add the next ones.

Fixed fee, quoted in writing

Confirmed after a short scoping call. No open-ended hours.

Monthly. Cancel any month.

  • Monitoring, fixes, and tuning for everything deployed
  • A monthly report against the Audit baseline
  • New automations added in priority order
  • On call for the decisions you would rather not make alone

Two ways to pay for the ongoing work. You choose.

Flat fee

A fixed monthly fee. You keep every dollar the work produces.

Best when you want a known cost and no one else looking at your books.

Outcome-linked

A lower base, plus a capped share of gains measured against your baseline.

Available when I am connected to your CRM and billing, so the numbers come straight from the source. The Audit sets the baseline, and the terms are in writing before work starts.

Free · 10 minutes

Is your business ready for AI?

Eight plain questions. You get a score, the areas to fix first, and the next step that fits.

0 of 8 answered

  1. 01How much of the daily work is written down?
  2. 02Where do customer and billing records live?
  3. 03How many decisions wait on you?
  4. 04Do you know where the repeat work is?
  5. 05Can your tools talk to each other?
  6. 06Could you try a change without customers noticing?
  7. 07How would your team react to AI doing part of the work?
  8. 08Do you know your numbers on the work AI would touch?

Answer all 8 to see where you stand and what to do first. Nothing is stored or sent.

Engagements

Four more 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

On-Demand Officer 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

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

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

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.

  • Technology executive leadership
  • Health-tech infrastructure
  • AI architecture and governance
  • Air Force veteran
  • Seven Gates leadership framework

Ask me directly

A direct line, and the playbooks.

Post the question in the community and get an officer-level answer. The playbooks come from the same deployments, for teams that want to do the work themselves.

Your Chief AI Officer

on Skool

The playbooks, templates, and lessons from real deployments, taught in the open.

  • A classroom of step-by-step lessons, built from real client work
  • Templates and checklists you can use the same day
  • Monthly live office hours
  • A room of owners doing the same thing, without the hype

Opening soon. Follow on any channel below to hear first.

Channel memberships

on YouTube

Back the channel and get members-only streams, videos, and early access. Perks for each level are listed on YouTube.

  • Observe$5.99 / month
  • Engage$9.99 / month
  • Influence$14.99 / month
  • Master$29.99 / month

Ready to move on AI with a steady hand?

One conversation. No deck required. We will know quickly whether there is a fit.