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, a tribal-knowledge inventory, an AI-native role design, and a 90-day execution plan. Not a deck. The redesign in writing.
TL;DR · 60-second read
What you walk away with
The org redesign in writing. Decision-flow map, role design, 90-day plan. Survives CFO scrutiny.
- Who it's for
- COOs, VPs of Ops, and CEOs in pilot purgatory or under board AI pressure. Mid-market service firms, $5M to $200M ARR.
- Format
- 3 to 4 week diagnostic. Four artifacts delivered.
- Investment
- Quoted in writing within 48 hours.
- Next step
- Book the Audit
Who it's for
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.
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.
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.
The frameworks
Two anchor ideas. Both public. Both load-bearing.
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.
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.
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.
What you get
Four artifacts. Each one usable on its own. Stronger as a set.
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.
The tribal-knowledge inventory
Captured in weeks 1-2 through interviews and observation. Each entry names source, decision context, the unwritten rule, the why. Becomes the input layer for the role redesign and the agent design. Humans search it. Agents act on it. Future hires ramp from it.
The AI-native role design
Jobs that change. Roles that disappear. Roles that emerge. Where headcount-to-output breaks. Every redesigned role names a human accountable for the AI-augmented work it produces. Agents do work. Humans own outcomes. Built so your CHRO and COO run the conversation without translation.
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.
The engagement
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.
Weeks 1-2 · Inventory and interviews
Map the workflows and capture the tribal knowledge
Inventory pilots, tools, vendors. Interview operators, sponsors, and the people whose roles change first. Pull tribal knowledge out of senior heads into the inventory: source, decision context, unwritten rule, the why. This becomes the input layer for the redesign.
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.
The outcome
Walk out with the redesign. Six months later, see the shift.
Week 4 · You walk out with
The redesign in your hands
Four 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."
FAQ
Frequently asked questions
What is an AI-Native Org Audit?
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 four artifacts: a decision-flow map, a tribal-knowledge inventory, an AI-native role design, and a 90-day execution plan. Not a strategy deck. The redesign in writing.
How much does the AI-Native Org Audit cost?
Scoped against company size, surface area, and number of stakeholders. 3 to 4 weeks end to end. Four artifacts delivered. Quoted in writing within 48 hours of the discovery call.
Who is the AI-Native Org Audit for?
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.
Is this just a strategy deck?
No. It's four artifacts: a decision-flow map, a tribal-knowledge inventory, 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.
Do you actually build during this engagement?
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.
What if our pilots haven't started yet?
Better. Easier to design the org than unwind a stalled portfolio.
How is this different from a McKinsey AI assessment?
Director-altitude plus patterns shipped daily, from the same operator. The deliverable is the redesign in writing, not a deck pointing at one.
Can we use the output without buying a follow-on?
Yes. Most clients graduate to Fractional because they want the same operator running the redesign. Many run it themselves.
We already hired the Head of AI. Is this still useful?
Yes. Often Phase 1 of the Fractional engagement. Gives the lead an org redesign to lead from, instead of a portfolio with no map.
What's your guarantee on this engagement?
Two guarantees. SKU guarantee: if the four artifacts (decision-flow map, tribal-knowledge inventory, AI-native role design, 90-day execution plan) are not signed off by your named COO and CFO in the week-4 readout, the final 50% invoice is waived. Umbrella guarantee on every engagement: a 14-day mutual exit. Either party can end the engagement inside the first 14 days. Days worked are billed at the agreed day rate. No further commitment.
What's included
What's included beyond the four artifacts.
Bonus 01
30 days of Slack and email access post-readout
Direct access for follow-up questions. Pushback rehearsal before the board sees it.
Bonus 02
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
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.
Capacity
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.
The guarantee
The guarantee.
If the four artifacts don't land with your COO and CFO in writing, you don't pay the back half. That removes the "expensive deck" risk from the buyer's pile.
AI-Native Org Audit guarantee
Sign-off or 50% waived
If the four artifacts (decision-flow map, tribal-knowledge inventory, AI-native role design, 90-day execution plan) are not signed off by your named COO and CFO in the week-4 readout, the final 50% invoice is waived.
Umbrella · Every engagement
14-day mutual exit
Every engagement carries a 14-day mutual exit. Either party can end the engagement inside the first 14 days. Days worked are billed at the agreed day rate. No further commitment.
Name what to redesign
Name what to redesign before you ship more AI.
30 minutes to see if the audit fits. 3 to 4 weeks.