AI Strategy Red Teaming
The red team before the green light.
Independent, intelligence-grade review of AI decisions before you spend. Built for mid-market executives and pre-fundraise founders who need more than a vendor's word.
Taking select Q3 2026 engagements
The failure is almost never the technology. It is judgment.
Untested assumptions. Unvalidated ROI math. Vendor claims nobody pressure-tested. AI spend is outrunning AI judgment, and boards are starting to ask questions that gut feel cannot answer.
Most leaders don't have a decision framework that survives contact with an AI vendor's pitch deck. They have a gut feeling, a budget, and a calendar.
We help you make the right AI decision for your organization, not the easy one.
We don't build AI. We don't train teams. We don't sell implementation. We apply Intelligence Community Structured Analytic Techniques to the AI decision itself, before the contract is signed. The output is an executive decision memo your board can defend, not another slide pile.
"It's not AI, and that's okay."
Sometimes that is the finding. We say it when the evidence says it.
Four structured analytic techniques, built where being wrong is expensive.
Structured analytic techniques are the disciplined methods intelligence agencies use to test high-stakes decisions under uncertainty. The four below are the ones we lead with, drawn from a broader intelligence-community toolkit. We apply them to the specific AI decision you are facing.
Key Assumptions Check
What beliefs must be true for this AI initiative to succeed, and which of them are actually fragile?
Analysis of Competing Hypotheses
Of the three or four strategic paths available, which one does the evidence actually support?
What-If Analysis
What are the plausible failure scenarios, their triggers, and their early warning signs?
Red Team Analysis
How would a competitor, a skeptic, or an adversary break this plan? What is the strongest case against it?
Intake
Structured executive interview. Evidence Matrix built. Vendor claims, ROI assumptions, architecture, budget, and timeline extracted and tagged as Strong, Moderate, or Weak evidence.
Analysis
All four SATs applied. Synthesis Matrix scoring the initiative across six dimensions: problem urgency, AI necessity, data readiness, technical feasibility, commercial viability, execution risk.
Delivery
Executive decision memo, 5 to 8 pages. Decision Risk Matrix. A live walkthrough of the findings, and one follow-up call within 14 days.
Every engagement ends in a straight recommendation
Two engagements. Fixed scope, fixed price, fixed timeline.
Mid-Market AI Adopter Assessment
For $10M to $500M revenue companies with an active AI decision or an in-flight initiative. The full 10-day Red Team Assessment, ending in a decision your board can defend.
- Evidence Matrix with source citations
- Key Assumptions table with priority ratings
- ACH scoring matrix and What-If scenario table
- Synthesis Matrix and Decision Risk Matrix
- Executive decision memo, 5 to 8 pages
- 30-day next steps and one follow-up call
Pre-Fundraise Startup Stress Test
For founders with an AI-centric deck preparing for seed or Series A. A condensed 5-day engagement focused on investor-grade defensibility of the AI claims in the deck.
- Founder briefing memo, 3 to 5 pages
- AI claim risk register
- Remediation list ranked by investor-perception impact
- One follow-up call inside 14 days of delivery
Pricing is published on purpose; you should not have to ask. We take a maximum of two concurrent engagements. Scope beyond the defined deliverables is a written change order, agreed before the work.
Methodology from a world where untested assumptions cost more than money.
Founder
Ben Brown. Two decades pressure-testing high-stakes decisions across U.S. military intelligence and special operations. The methods behind Ayo Advisors come from that world, adapted for the boardroom.
Methodology Pedigree
The four Structured Analytic Techniques come from intelligence-community analytic tradecraft, built where being wrong is expensive. Ayo Advisors is the only firm we know of applying them directly to commercial AI decisions.
Adversarial by Design
No implementation partners. No vendor referral fees. No platform to sell. That independence is the product; our only incentive is to break your plan before your competitor does.
This works when you want the plan challenged, not confirmed.
Who this is for
- Mid-market executives with an AI project on the table or mid-flight.
- Pre-fundraise founders whose deck will face AI-specific due diligence.
- Boards and investors who want the rationale documented before capital moves.
Who this is not for
- Companies looking for someone to build or deploy AI.
- Teams looking for a rubber stamp on a decision already made.
- Buyers who need AI training, enablement, or change management.
Put the decision on the table.
If there is an AI decision on your table this quarter that a hard second look would de-risk, that is the work we do. One email starts it; a scoping conversation and a fixed-price proposal follow within days, not weeks.
Taking select Q3 2026 engagements
Direct line to the founder
Goes straight to Ben's inbox. No newsletter, no sequence, no obligation.