About
Morris Stern. Technology executive, Winnipeg.
VP of Retail Technology, previously VP of Retail Systems. 15+ years leading enterprise technology across Canadian and US operations: ERP, POS, payments, integration, store systems, healthcare IT, and AI adoption. The defining program: a 265-store, nine-month platform conversion, delivered on time and on budget.
The short version
I am a lifelong Winnipegger. I studied here, built my early career here, and still live here. Over the last several years the work drifted south: first as VP of Retail Systems for a cross-border retail group running 184 locations in Canada and the US, then through a divestiture to one of North America’s largest furniture and home goods retailers. The buyer standardized on the platform my team built and retained me to lead the conversion of both estates onto it, 265 stores in nine months, and I serve as VP of Retail Technology, working remotely from Winnipeg. I am now refocusing on the Manitoba market.
The record was built in high-volume retail because retail punishes weak technology leadership faster than almost any other industry. When the ERP stumbles, stores stop selling the same day. That environment taught me what it looks like when a POS rollout fails at go-live. When an ERP migration creates data quality debt that takes two years to unwind. When integration complexity quietly slows every new initiative. And how to prevent those outcomes before they happen.
The disciplines transfer directly to any enterprise that runs on systems it cannot afford to break: ERP and core platforms, integration architecture, payments, vendor governance, delivery governance, and AI governance. My delivery experience also spans provincial healthcare infrastructure, where I directed 50+ concurrent ICT capital projects across hospital systems, and manufacturing, where I built the digital commerce and BI foundations of a North American manufacturer.
I also take on select advisory engagements through Stern Technology Advisory. There is no team behind the brand and no vendor incentive behind the advice.
Experience
Where the record comes from
Direct accountability for the systems, teams, vendors, and go-live decisions that most technology recommendations only describe from the outside. Employers, titles, and dates are on the executive profile.
Retail technology leadership
VP of Retail Systems, then VP of Retail Technology
Led ERP, POS, store systems, ecommerce, payments, ESL, and integration programs for a 184-location cross-border group, then the combined 265-store, roughly $3B network, including its nine-month platform conversion.
Capital infrastructure
Program Director, provincial ICT capital projects
Directed 50+ concurrent healthcare ICT capital projects across hospitals and health regions with governance for budget, schedule, and quality.
Manufacturing and commerce
Head of IT and business solutions
Launched DTC and B2B marketplace channels for a North American manufacturer, integrated EDI and commerce workflows, and built executive sales and inventory reporting.
Select advisory
Stern Technology Advisory
Select advisory engagements for retailers, manufacturers, and private equity operators on modernization decisions, without vendor incentives.
How I work
Four principles that shape every program, in an executive seat or an advisory one.
01
Clarity first
Define the outcome and the constraints before recommending a path. Strategy without operational reality is expensive.
02
Practical architecture
Reduce complexity and improve data trust. The best architecture is the one your team can govern and your vendors can execute.
03
Governance that respects operations
Staged delivery, readiness checks, and decision cadences designed around operational uptime, seasonal peaks, and mission-critical constraints, not just project timelines.
04
Adoption is part of delivery
Store readiness, training strategy, and stabilization governance are built into the program plan from day one.
Areas of expertise
Executive background
The full career record
Employers, titles, dates, program outcomes, and the mandates I am focused on. Written for recruiters, hiring committees, and boards.
Common questions
Roles, advisory, and independence
- Is Morris available for executive roles?
- Yes. Morris is focused on VP of Technology, CTO, CIO, and Chief Digital Officer mandates, with a Winnipeg and Manitoba focus, and remains credible for US retail and enterprise technology leadership. The executive profile page has the full career record.
- Does Morris still take advisory work?
- Selectively. Advisory engagements run through Stern Technology Advisory and are scoped to a specific decision: an ERP direction, a program reset, a diligence read, or an architecture review. There is no team behind the brand. Every engagement is Morris directly.
- Is the advice independent of software vendors?
- Yes. No software resale, no referral fees, and no implementation partner relationships influence recommendations. Vendor and systems integrator decisions are evaluated against business fit, operating constraints, integration risk, and total cost.
Talk to Morris
Executive search, board inquiry, or a technology decision that needs a second set of eyes.