An AI roadmap tied to your P&L, not a slide deck.
We give mid-market leadership teams the strategy layer for AI: an honest readiness assessment, vendor-neutral tool analysis, a prioritized use-case roadmap with ROI projections — and, when the need is ongoing, a fractional Chief AI Advisor at the leadership table.
In one sentence: AI strategy here means deciding — with evidence — where AI pays off in your business, which tools to use, and what has to be fixed first, delivered as a 12–24 month roadmap your team can execute, with executive advisory available on a fractional basis.
Book a call about ai strategyThe problem: activity without a thesis
Most mid-market AI efforts start with a tool, not a business case. Someone buys licenses, a pilot launches in one department, and six months later nobody can say what it changed. Meanwhile vendors keep pitching, employees adopt whatever they like, and the board keeps asking for the AI story.
The missing piece isn't enthusiasm — it's a thesis: which workflows in this company can AI measurably improve, what do those improvements earn, and what operational groundwork does each one require. Without that, AI spend is guesswork.
The approach: assess, evaluate, prioritize
Readiness assessment
Stakeholder interviews plus a working review of your infrastructure, data, security posture, and identity controls. Not a survey — an operator reading your environment the way a diligence team would.
Vendor-neutral tool analysis
Structured evaluation of the AI tools and platforms relevant to your use cases — capability, security posture, data handling, pricing, and lock-in risk. Vendor-neutral, so the recommendation is the one that's right for you.
Use-case portfolio
Candidate use cases scored on value, feasibility, and risk — then sequenced so early wins fund and de-risk the harder ones.
Roadmap with ROI projections
A 12–24 month plan with owners, dependencies, cost ranges, and the operational prerequisites (data, security, access) called out per initiative.
Operating model design
Roles, decision rights, intake, and steering cadence for AI — sized for a mid-market company, not copied from an enterprise playbook.
Ongoing executive advisory
When the AI agenda needs a standing owner, a fractional Chief AI Advisor joins your leadership rhythm — a part-time AI executive, not a full-time hire.
Advisory capabilities
Eight ways the strategy practice shows up — engage one, several, or the full arc.
Executive AI Strategy
A leadership-level thesis on where AI earns its keep — connected to the operating plan and the P&L, so every initiative has a business owner and a number attached.
AI Readiness & Maturity Assessment
Stakeholder interviews, a working review of infrastructure, data, security, and identity, and a scored six-dimension maturity baseline. Start with the free online diagnostic.
AI Executive Workshops
Half- and full-day working sessions that bring your leadership team to a shared, realistic view of what AI changes for the business.
Fractional Chief AI Advisor
A part-time AI executive in your leadership rhythm: owns the AI roadmap, evaluates vendors, and carries the board's AI narrative. AI-only scope — for full technology ownership, see Fractional CIO.
Investment Prioritization & Business Cases
Candidate use cases scored on value, feasibility, and risk, then sequenced — with ROI projections and cost ranges your CFO can budget against, per initiative.
AI Cost & Consumption Modeling
What usage-based AI pricing actually costs at your scale: token and license economics modeled per use case, so the business case survives contact with the invoice.
AI Operating Model Design
Roles, decision rights, intake paths, and steering cadence for AI — designed for mid-market headcount and speed.
Executive Roadmaps
A 12–24 month plan with owners, dependencies, and the operational prerequisites called out per step.
How the engagement runs
A typical engagement runs three to five weeks, fixed-fee.
- Week 1
Discovery
Stakeholder interviews and a working review of infrastructure, data, security, and identity.
- Weeks 2–3
Analysis
Vendor-neutral tool evaluation and use-case scoring against your P&L.
- Week 4
Roadmap
A sequenced 12–24 month plan with owners, costs, and prerequisites.
- Week 5
Readout
A leadership working session to pressure-test and finalize the plan.
What you walk away with
Every engagement ends in artifacts you own — not a verbal debrief.
- AI readiness assessment report — infrastructure, data, security, and identity findings
- Vendor-neutral tool evaluation matrix with scored recommendations
- Scored use-case portfolio (value × feasibility × risk)
- 12–24 month roadmap with owners, dependencies, and cost ranges
- ROI projections your CFO can budget against
- Executive readout deck and working session
The outcome, measured
A defensible answer to 'what should we do about AI' — specific tools, specific workflows, specific numbers — plus a clear-eyed list of what must be fixed before each step. Many clients continue into implementation with CSM; the roadmap is written so any competent team could execute it.
- A defensible answer to “what should we do about AI” — specific tools, workflows, and numbers
- A prioritized sequence where early wins fund and de-risk the harder initiatives
- A clear list of operational prerequisites to fix before each step
- A roadmap any competent team can execute — no lock-in to CSM
Questions buyers actually ask
What does an AI readiness engagement cost?
Pricing depends on company size and scope, and is set on the intro call. As a reference point, a full readiness assessment and roadmap for a mid-market company is a fixed-fee project measured in weeks, not months — and materially less than a Big 4 engagement. The online AI Maturity Diagnostic is free and takes about five minutes.
We've already bought AI tools. Is strategy still useful?
Yes — arguably more so. The assessment evaluates what you already own against your actual use cases, identifies overlap and gaps, and frequently finds licensed capability going unused. The roadmap then builds around what's worth keeping.
How is this different from a vendor's free AI assessment?
A vendor's assessment exists to sell you that vendor's platform. We evaluate tools against your requirements — vendor-neutral, including the option of recommending nothing new.
Related services
AI Transformation Program
Our flagship program: sixteen phases across four waves that take a mid-market company from honest assessment to scaled, governed, measured AI.
AI Governance, Security & Risk
Usage policy, identity and access controls, data protection, and audit-ready governance so AI adoption never becomes a liability.
Talk to an operator, not a salesperson.
Engagements typically begin with a 30-minute call and, where it fits, an AI readiness assessment. No retainer required — the first conversation is free.