Strategic AI Advisory for Mid-Market CEOs
Most AI advisory is built for Fortune 500 CIOs or venture-funded startups. This is built for the CEO of a $10M–$1B company who needs to make capital allocation decisions on AI in the next two quarters and have a defensible answer for the board. No frameworks built in a vacuum, no transformation theater — direct work, delivered personally by Shawn Moore, on the actual decisions in front of you.
Who this is for
- CEOs of $10M–$1B companies evaluating AI investment for the first time, or recovering from a stalled pilot portfolio.
- PE-backed leadership teams under pressure to show AI traction without sacrificing operating discipline.
- Founder-CEOs whose board is asking 'what's our AI strategy?' and the answer needs to land in writing.
- CFOs and COOs who are co-sponsoring AI initiatives and need a partner the executive team will actually listen to.
What you get
- A scored AI Readiness Assessment across the six pillars (strategy, data, infrastructure, governance, talent, culture) with a sequenced remediation plan.
- A capital allocation framework that maps every candidate AI investment to build, buy, or wait — with three-year TCO modeling.
- A board-ready AI strategy memo: positioning, priorities, governance posture, and the two-year roadmap, in language a non-technical board can defend.
- Vendor selection support for the two-to-four AI investments you actually move forward with — including reference call scripts and contract red flags.
- Direct access between sessions for the inevitable curveballs (a vendor pitch, a board question, a competitor announcement).
Methodology
Diagnose before prescribing
Engagements start with a structured diagnostic of your current AI posture — anchored in the six-pillar AI readiness framework, not a survey. The output is a written assessment you can hand to anyone on the board and they will understand exactly where you stand and why.
Allocate capital like a portfolio
Every candidate AI initiative is plotted using the build vs buy vs wait matrix against strategic differentiation and time-to-value, then stress-tested against three-year TCO. The output is a ranked portfolio with named owners, reconsideration triggers, and a clear answer for the things you are choosing not to fund.
Build the governance scaffold first
Most mid-market AI failures are governance failures, not technology failures — the four failure modes are well documented. We design the lightweight oversight model — accountable owners, escalation paths, kill criteria — before the first dollar of pilot capital is committed.
Stay through execution, not just strategy
The strategy memo is the start, not the deliverable. Ongoing engagements include monthly working sessions through the first two-to-three implementations, when most of the real decisions get made and most consultants have already moved on.
Engagement model
- Diagnostic Sprint
- Six weeks. Readiness assessment, capital allocation framework, and board-ready strategy memo. Fixed scope, fixed fee.
- Ongoing Advisory
- Twelve-month retainer. Monthly working sessions with the executive team plus on-demand access for vendor decisions and board prep.
- Board Engagement
- One-time board working session: state of AI in your industry, your readiness, the recommended posture. Two hours, no slides.
- Geographic scope
- United States and Canada. Hybrid delivery — quarterly on-site working sessions, monthly virtual.
Frequently asked questions
Related insights
The AI Savvy Readiness Framework
The six-pillar assessment used in every diagnostic sprint. Score strategy, data, infrastructure, governance, talent, and culture before committing capital.
Read more ResearchWhy Enterprise AI Pilots Fail
The four-failure taxonomy that drives our pilot portfolio review. Diagnose before you fund the next experiment.
Read more MethodologyThe Build vs Buy vs Wait Matrix
The capital allocation framework behind our vendor selection support. Plot every AI investment against differentiation and urgency.
Read moreRelated services & resources
About Shawn Moore, 30-year operator-CEO
Three decades running P&L across digital strategy and AI. Why CEOs hire Shawn directly instead of a Big-4 team.
Read more Keynote SpeakingAlso available for keynote speaking
Bring the same frameworks to your next conference, board offsite, or PE portfolio convening.
Read moreReady to start the conversation?
Ninety minutes. No deck. We work the actual problem and you leave with a defensible next step.
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