Technology Executive · Winnipeg, Manitoba
Technology leadership from strategy to operational reality.
I am a Winnipeg-based technology executive with 15+ years leading ERP, M&A integration, retail systems, payments, and major transformation programs across Canada and the United States. Open to permanent executive mandates and select advisory work.
Winnipeg, Manitoba · Canada and United States
Published in
- 15+
- Years leading enterprise technology
- 50+
- Concurrent capital projects directed
- 2
- Countries of operating accountability
The record
Work I have led as the accountable executive.
Programs where the vendor calls, the go-live decisions, and the escalations landed on my desk. Client names, internal figures, and program details are withheld or generalized.
Post-acquisition platform conversion
Led a major post-acquisition platform conversion across a large North American retail network, moving two retail estates onto one surviving platform while every store kept trading. The cutover playbook built during the program made each successive store onboarding materially faster.
Read the conversion summaryStore systems and payments at chain scale
Modernized point of sale and payments across a multi-site chain, delivering material recurring payment savings, improving store-system resilience, and reducing support demand on the help desk.
Read the store systems summaryA multi-million-dollar ICT capital portfolio
Directed a multi-million-dollar ICT portfolio across more than 50 concurrent projects inside a provincial healthcare capital program, including two new-build hospitals in a regulated, audit-intensive environment.
Read the healthcare summaryHow I operate
Technology programs fail in predictable places. I plan for them.
Programs fail between strategy and operations
The deck says modernize. The store still has to sell on Saturday, the plant still has to ship, the claims system still has to pay. I sequence technology change around the operating reality, not the project plan.
Vendors manage to their contract
Left alone, every vendor and systems integrator optimizes for their own scope. Somebody on the buy side has to own the outcome. That governance is a core part of how I run programs.
Adoption decides the outcome
A system nobody uses correctly is a failed system, whatever the status report says. Readiness, training, and stabilization are built into my programs from day one, not added in the last six weeks.
About
A Winnipegger with a cross-border record.
I am a lifelong Winnipegger. Over the last several years my work drifted south: first as Vice President of Retail Systems for a cross-border retail group operating in Canada and the US, then through a divestiture to one of North America’s largest furniture and home goods retailers, where I was most recently Vice President of Retail Technology, working remotely from Winnipeg. That engagement concluded in July 2026. I am now focused on the Manitoba market first.
Retail is where much of the record was built, because high-volume retail operations expose weak technology leadership quickly. The disciplines transfer: ERP and enterprise systems, integration architecture, payments, vendor governance, delivery governance, and AI governance. Before retail, I directed more than 50 concurrent ICT capital projects for a provincial health system and ran IT and business intelligence for a North American manufacturer.
Permanent executive leadership is the primary path. I also take on select advisory work through Stern Technology Advisory.
What colleagues say
“Driving complex projects in a simple and structured way is one of his greatest strengths. Morris is a real team motivator, never afraid to take important actions for the benefit of the company. He is committed to achieving excellent results while fostering collaboration and demonstrating a strong sense of availability.”
“He’s been able to get into some of the most complex technologies and sometimes ridiculously convoluted systems, and make sense of them and then break them down in order to improve and streamline them. I’ve also seen first-hand how he can break strategy down into actionable plans and see them through to execution.”
Selected work
Four programs, each summarized as context, role, actions, and outcome. All were completed in an executive operating role.
M&A Platform Conversion
A major post-acquisition platform conversion across a large North American retail network, run on readiness gates, wave sequencing, and a cutover playbook that improved with every wave.
Executive role · Store systemsStore Systems, Payments, and Digital Price Tags
Point of sale, payments, and shelf-edge pricing modernized across a multi-site chain, with material recurring payment savings and improved store-system resilience.
Executive role · Capital programsProvincial Health System ICT Capital Portfolio
A multi-million-dollar ICT portfolio across more than 50 concurrent projects and two new-build hospitals, governed through a distributed, fully remote delivery model.
Executive role · CommerceDigital Commerce and Business Intelligence
Direct-to-consumer and marketplace channels built for an established manufacturer, supported by ERP, EDI, and executive reporting that changed how inventory decisions were made.
Insights
Articles on enterprise systems, store technology, AI governance, and modernization decisions. Published here, in CIOReview and Retail Tech Insights, and on LinkedIn.
FAQ
Common questions
- Who is Morris Stern?
- Morris Stern is a Winnipeg-based technology executive and advisor with 15+ years leading ERP, M&A integration, retail systems, payments, and major transformation programs across Canada and the United States. He was most recently Vice President of Retail Technology for a large North American home furnishings retailer, and before that Vice President of Retail Systems for a cross-border retail group.
- What is Morris focused on now?
- Permanent executive leadership mandates are the primary focus: VP of Technology, CTO, CIO, and Chief Digital Officer roles, Winnipeg and Manitoba first, with remote and hybrid arrangements across Canada and the United States. Select advisory work is secondary.
- What is Stern Technology Advisory?
- Stern Technology Advisory is the select advisory practice Morris runs alongside his executive career. It covers transformation and ERP advisory, retail systems and store technology, and program stabilization and executive oversight. Engagements are scoped to a specific decision, and there is no team behind the practice.
- Does Morris work outside retail?
- Yes. Retail is where much of the record was built, because high-volume retail operations expose weak technology leadership quickly. The disciplines transfer: ERP and enterprise systems, integration architecture, payments, vendor governance, delivery governance, and AI governance. His program delivery experience also spans provincial healthcare infrastructure and manufacturing.
Start with the profile.
The executive profile carries the career record, the mandates I am focused on, and how I lead programs. If the fit looks right, the next step is a conversation.
Based in Winnipeg · Canada & US