Do you take Winnipeg clients in person?

Yes. Shawn Moore travels to Winnipeg on request for multi-day working sessions. Most engagements combine on-site working sessions in Winnipeg Capital Region with weekly video steering meetings between visits.

What does an engagement look like for a mid-market Winnipeg 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.

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Winnipeg Capital Region

AI Consultant for Winnipeg and Winnipeg Capital Region Mid-Market CEOs

AI Savvy provides strategic AI advisory to Winnipeg and Winnipeg Capital Region 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 Winnipeg on request for multi-day working sessions.

Why Winnipeg Capital Region mid-market is at an AI inflection point

Winnipeg is the transportation and agri-food gateway of the Canadian Prairies, 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, while Microsoft's June 2025 Canadian SMB Report put national adoption at 71% — with 90% adoption among digital-native firms.

Winnipeg's mid-market economy runs on transportation, insurance, agri-food, and manufacturing — sectors where operational AI use cases produce clean, measurable ROI. The University of Manitoba's AI programs and a growing base of North Forge–incubated companies sit alongside the traditional industrial base.

What we do for Winnipeg 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.

Manitoba-specific considerations

Manitoba's PIPA is currently limited in scope; PIPEDA governs most private-sector data handling. Public sector, health (PHIA), and insurance regulators set additional layers for common Winnipeg mid-market use cases.

Winnipeg's talent pool is strong on operational and analytical roles and thin on senior AI strategy owners. Mid-market boards are increasingly asking for outside advisory to fill the gap.

How we work with Winnipeg clients

Most Winnipeg 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 Winnipeg on request for multi-day working sessions. Engagements can be invoiced in CAD or USD; corporate accounts payable in either currency are routine.

Industries we focus on in Winnipeg Capital Region

Transportation and logistics

Winnipeg's transportation cluster applying AI to routing, fleet, and freight-margin optimization.

Insurance and financial services

Manitoba-chartered mutuals and cooperatives navigating OSFI E-23 alignment where federally regulated.

Agri-food and manufacturing

Prairie agri-food processors and manufacturers deploying AI for demand planning, quality, and traceability.

Foundational reading before we talk

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

Frequently asked questions

Book a Winnipeg 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.

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