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.

Responsibilities

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

Requirements

5+ years of experience in strategy, digital transformation, or internal consulting roles; Strong experience in digital strategy; Bachelor’s degree in a related field; Strong influencing skills without formal authority; Clear and effective communicator, both written and verbal; Fully bilingual (English/French), able to collaborate across Canada

Nice to have

Roadmap exposure

Benefits

Ultimate Flexibility: Enjoy a hybrid work environment that ensures the perfect balance between work and personal life; Well-Being First: Access a comprehensive benefits program designed to take care of you; Flexible Time Off: Paid leave, sick days, and vacation time to recharge and spend quality time with loved ones; Exclusive Discounts: Enjoy 50% off regular-priced items from PENN. Penningtons, Reitmans, and RW&CO; Referral Rewards: Refer your professional network and earn a bonus for helping us grow our talented team; Growth opportunities: Annual bonuses, career advancement, and tuition reimbursement to help you reach your professional goals