Product Owner

We are seeking a strategic and hands-on Product Owner - Business Systems to own the roadmap and backlog for a core business capability (e.g., Sales Enablement, Purchasing & Logistics, or Order Management & Finance).

This is not a ticket-taking role. You will challenge current-state processes, identify meaningful improvement opportunities, and partner across business and technology teams to deliver measurable outcomes. You’ll play a key role in shaping how systems, data, and workflows drive operational excellence and user experience.

As a Product Owner, you will

Product Strategy & Roadmap

• Develop and maintain a clear product roadmap balancing immediate operational needs with long-term transformation goals
• Align roadmap priorities to business strategy, KPIs, risk, and dependency considerations

Process & Solution Improvement

• Identify gaps across processes, data, controls, usability, and automation
• Evaluate friction points for customers and employees and propose scalable improvements
• Challenge stakeholders to rethink and improve processes instead of replicating legacy approaches

Backlog Ownership & Delivery

• Own and prioritize the product backlog based on business value, urgency, and effort
• Translate business needs into:
• Requirements and process maps
• User stories and acceptance criteria
• UI/UX expectations and measurable outcomes

Cross-Functional Collaboration

• Partner closely with Project Managers, Developers, Solution Architects, D365 Admins, and Data teams
• Facilitate workshops, backlog refinement sessions, demos, and decision forums
• Ensure alignment across business and technical stakeholders

Testing & Release Execution

• Participate in system testing and lead/support UAT
• Validate delivered solutions against requirements before release
• Coordinate release readiness, including training, documentation, and adoption activities

Performance & Adoption

• Measure outcomes against defined KPIs
• Ensure delivered solutions drive real business improvements
• Support post-launch optimization and continuous improvement

To be successful in this role, you bring

• 5+ years in product ownership, business analysis, enterprise systems, or digital transformation
• Proven ability to prioritize competing demands and connect technology to business outcomes
• Strong business analysis skills:
• Process mapping
• Requirement definition
• User stories and acceptance criteria
• Benefit measurement
• Excellent stakeholder engagement skills with the ability to influence and challenge effectively
• Experience with testing, UAT, and validating delivered solutions
• Strong communication skills-able to translate between business and technical teams
• Comfortable working with data and KPIs to drive decisions and measure success
• Solid understanding of UI/UX principles in business systems

Bonus points

• Experience with Microsoft Dynamics 365 (Finance & Operations, Commerce, CRM), Power Platform, or similar enterprise systems
• Background in retail, supply chain, logistics, finance, customer service, or sales enablement
• Familiarity with Agile delivery practices and backlog management tools
• Experience with process mapping, journey mapping, wireframing, or prototyping
• Exposure to change management, training, adoption, and post-launch performance tracking

Who You’ll Work With

• Senior Director, Business Enablement, Automation & Data
• Business leaders, SMEs, and frontline teams
• Other Product Owners and Enablement team members
• IT teams including developers, QA, architects, and operations
• Data, analytics, finance, HR, and external partners/vendors

Work Environment

• Hybrid work environment with regular in-person collaboration sessions
• Standard business hours with occasional support during releases or critical events
• Minimal travel; occasional visits to stores, distribution centres, or business sites may be required

Why Join Trail?

• Competitive salary + extended health benefits
• Generous employee appliance discounts
• Opportunities for career growth and development
• Collaborative, team-oriented culture with events and volunteer programs
• Opportunity to impact a trusted Canadian brand at scale