01 · Bucket
Pilot Purgatory
Pilots shipped. Some worked, most stalled. Board wants throughput. Nobody knows if the answer is more pilots, different vendors, or a different org.
Diagnostic · 3 to 4 weeks
Your AI pilots stalled because your org chart didn't change. The audit names what to redesign.
A 3 to 4 week diagnostic for COOs and VPs of Ops carrying AI pressure. You walk out with a decision-flow map, an AI-native role design, and a 90-day execution plan. Not a deck. The redesign in writing.
§01
The COOs booking this call land in one of three buckets.
Without the audit, you ship more pilots and more tools. With it, you ship the redesign that makes everything after it cheaper.
02 · Bucket
Board Pressure, No Pilots
Board is asking about AI. You haven't started. Spending six figures on tools before redesigning the org reads like burning money in public.
03 · Bucket
Already Hired the Head of AI
The lead is in seat. They need a peer at altitude, not another implementer. Phase 1 of the Fractional engagement.
§02
Two anchor ideas. Both public. Both load-bearing.
01 · Anchor
Bain's operating-model thesis
AI decouples headcount from output. Old math (more revenue, more hires) breaks. New math needs a different planning artifact. The audit produces it.
02 · Anchor
Anthropic's manager-IC principle
AI lets one person operate as both manager and IC. The middle layer compresses. The audit maps where compression happens in your business.
03 · Anchor
Director altitude, not implementer altitude
Written for the COO conversation, not the engineering standup. Defensible to your CEO, board, and CFO in the same week.
§03
Three artifacts. Each one usable on its own. Stronger as a set.
01 · Artifact
The decision-flow map
Current vs target flows for the workflows under pressure. Every decision named: who owns it today, who owns it after, where agents and humans co-act, where humans handle exceptions. A decision-rights artifact.
02 · Artifact
The AI-native role design
Jobs that change. Roles that disappear. Roles that emerge. Where headcount-to-output breaks. Built so your CHRO and COO run the conversation without translation.
03 · Artifact
The 90-day execution plan
Sequenced moves with owners and dependencies. Which pilots to restart, retire, or absorb. What to build, buy, defer. The plan a Director of AI would run on day one.
§04
3 to 4 weeks. Me plus your COO or VP Ops plus one finance or HR partner.
Working sessions plus interviews with 10 to 15 operators. Artifacts land in your next operating cadence, not a quarter from now.
Week 1 · Inventory and interviews
Map the workflows under pressure
Inventory pilots, tools, vendors. Interview operators, sponsors, and the people whose roles change first.
Week 2 · Decision-flow mapping
Draw current and target flows
Mark friction, duplicated work, dropped handoffs. Draw target flows with agents and humans as co-actors. Stress-test against failure modes.
Week 3 · AI-native role design
Translate flows into roles
Jobs that change, roles that disappear, roles that emerge. Name the headcount-to-output assumptions that break.
Week 4 · Execution plan and handoff
Sequence the redesign
Owners and dependencies. Package the artifacts. Walk the executive team through the defense. Hand off.
§05
Walk out with the redesign. Six months later, see the shift.
Week 4 · You walk out with
The redesign in your hands
Three artifacts plus the language to defend them to the board without resorting to "AI is important."
+6 months · Clients report
The shift
Stalled pilots restarted or got retired. Headcount plans rewrote around output. The Head of AI led a real org. The board stopped asking "what about AI" and started asking "what's next."
§06
Frequently asked questions
A 3 to 4 week diagnostic that maps the organizational redesign required to ship AI past the pilot stage. Anchored in Bain's headcount-to-output decoupling thesis and Anthropic's manager-IC compression principle. Deliverables are three artifacts: a decision-flow map, an AI-native role design, and a 90-day execution plan. Not a strategy deck. The redesign in writing.
$7-12k, scoped against company size, surface area, and number of stakeholders. 3 to 4 weeks end to end. Three artifacts delivered. Quoted in writing within 48 hours of the discovery call.
COOs, VPs of Ops, and CEOs in one of three buckets: pilots shipped but stalled (pilot purgatory), board pressure but no pilots yet, or a Head of AI in seat who needs a peer-altitude org redesign to lead from. Mid-market service firms, roughly $5M to $200M+ ARR.
No. It's three artifacts: a decision-flow map, an AI-native role design, and a 90-day execution plan. Your COO and CHRO use them in operating cadence. Your CFO uses them in planning. Your board sees the output of the redesign, not the deck about it.
No. Build happens inside Fractional Head of AI Transformation or Scoped AI Build. The audit tells you what to build, in what order, and why.
Better. Easier to design the org than unwind a stalled portfolio.
Director-altitude plus patterns shipped daily, from the same operator. The deliverable is the redesign in writing, not a deck pointing at one.
Yes. Most clients graduate to Fractional because they want the same operator running the redesign. Many run it themselves.
Yes. Often Phase 1 of the Fractional engagement. Gives the lead an org redesign to lead from, instead of a portfolio with no map.
§07
What's included beyond the three artifacts.
Bonus 01 · $2k
30 days of Slack and email access post-readout
Direct access for follow-up questions. Pushback rehearsal before the board sees it.
Bonus 02 · $1.5k
AI Readiness Scoring Rubric
6-dimension rubric used inside the engagement, with named failure modes per band. Re-run quarterly without re-engaging.
Bonus 03 · $1k
Vendor evaluation criteria template
Criteria I use to filter the AI vendor stack. Cost, lock-in, eval surface, integration cost, exit path. Yours before the next vendor pitch lands.
§08
Capacity is honest. ~4 active client commitments at a time.
I hold ~4 active client commitments across Fractional, Scoped Build, and Audit. Mix depends on what's already booked. The interview load requires my full attention. Engagements are picked, not sold.
Name what to redesign
Name what to redesign before you ship more AI.
30 minutes to see if the audit fits. $7-12k, 3 to 4 weeks.