Strategic Advisor - Digital Strategy

At a pivotal moment of transformation, Reitmans Canada limited – RCL is seeking a Strategic Advisor – Digital Strategy to partner directly with the Chief Digital and Customer Officer. This role is centered on shaping and advancing the organization’s digital strategy, while providing oversight and guidance on the digital roadmap to ensure alignment with strategic priorities.

This is a senior, high-trust role for someone who thrives in complexity and ambiguity, and who can bring clarity, structure, and focus to evolving digital initiatives. You will help define where the organization is going digitally—and ensure that the roadmap reflects and supports that direction.

As a Strategic Advisor, you act as both a thought partner and a strategic integrator. You help frame key questions, challenge and refine direction, and ensure that digital initiatives are aligned to a clear strategic narrative. You work across teams to connect strategy to execution, while maintaining a high-level view of the roadmap to ensure coherence, prioritization, and impact.

What You’ll Do

• Partner directly with the CDCO to shape, evolve, and articulate the digital strategy
• Define strategic priorities and guide decision-making to ensure alignment with business and customer objectives
• Provide strategic oversight of the digital roadmap, ensuring it reflects priorities, sequencing, and intended outcomes
• Translate strategy into clear direction, principles, and frameworks to guide teams
• Develop executive-level materials, including strategic narratives, briefs, and decision frameworks
• Create alignment across digital, brand, transformation, and corporate strategy teams
• Identify risks, gaps, and misalignments between strategy and roadmap, and recommend adjustments
• Work closely with the Chief of Staff and Transformation Office to ensure strategic consistency and momentum
• Support the evolution of the digital operating model, aligned to strategic priorities (not roadmap ownership)
• Strengthen governance and prioritization through data-driven frameworks to support effective decision-making