Do you take Chicago clients in person?

Yes. Shawn Moore travels to Chicago quarterly. Most engagements combine on-site working sessions in Chicagoland with weekly video steering meetings between visits.

What does an engagement look like for a mid-market Chicago company?

The typical sequence is a 2–4 week paid AI Growth Audit ($15K–$35K range), followed by a fixed-scope 90-Day Execution Blueprint ($25K–$50K range). Most companies decide on the long-term advisory shape — fractional CAIO, internal hire, or quarterly cadence — only after one full 90-day cycle.

Home

Chicagoland

AI Consultant for Chicago and Chicagoland Mid-Market CEOs

AI Savvy provides strategic AI advisory to Chicago and Chicagoland CEOs of $10M–$250M companies. Engagements include the AI Growth Audit, the 90-Day Execution Blueprint, and ongoing fractional Chief AI Officer support. Shawn Moore travels to Chicago quarterly.

Why Chicagoland mid-market is at an AI inflection point

Chicago is the Midwest's largest financial, insurance, and industrial mid-market, and its mid-market is in the middle of an uneven AI inflection. RSM's 2025 Middle Market AI Survey found 91% of mid-market organizations across the US and Canada now use generative AI in operations, but the same survey flagged that governance maturity and internal expertise still lag adoption sharply across every US metro.

Chicago is the Midwest capital of insurance, derivatives, industrial manufacturing, and B2B services — sectors where AI use cases produce measurable margin and where governance discipline is non-negotiable.

What we do for Chicago companies

Strategic Advisory →

Fractional CAIO retainers and 90-day blueprints with the operator in the room.

Keynote Speaking →

CEO-audience keynotes and board sessions on AI strategy and governance.

Executive Education →

Working-session programs that hand the methodology to your executive bench.

Illinois-specific considerations

Illinois's Biometric Information Privacy Act (BIPA) is the most consequential state biometric statute in the US and applies to any AI use case processing biometric identifiers. The Illinois AI Video Interview Act adds hiring-adjacent obligations. Insurance-sector AI use falls under the NAIC AI Model Bulletin as adopted by the Illinois DOI.

Chicago has strong operating and analytical talent and a persistent gap in executive-layer AI ownership at the CEO tier. Most engagements are about installing that layer.

How we work with Chicago clients

Most Chicago engagements run on a hybrid cadence: on-site working sessions when scope warrants, weekly video steering meetings, and async document review between sessions. Shawn Moore travels to Chicago quarterly. Engagements are invoiced in USD; Canadian entities of US clients can be billed in CAD on request.

Industries we focus on in Chicagoland

Insurance and financial services

Chicago insurers, exchanges, and wealth managers under NAIC AI Model Bulletin, SEC, and CFTC frameworks.

Industrial and manufacturing

Midwest industrial manufacturers applying AI to production, quality, and supply chain.

Professional services and healthcare

AmLaw and Big Four Chicago practices plus Chicago-area health systems navigating HIPAA and Illinois-specific rules.

Foundational reading before we talk

The AI Savvy Readiness Framework — the six-pillar diagnostic used in every Chicago engagement.
The 90-Day AI Execution Blueprint — the four-phase methodology we run in Chicagoland.
AI Consulting Cost Guide for Mid-Market CEOs (2026) — what an honest engagement should cost.

Frequently asked questions

Book a Chicago strategy call

Thirty minutes, no slides, no software pitch. Bring your AI portfolio, an active proposal, or a single decision on your desk. Leave with a written second opinion.

Book a Strategic Call