Director, Strategy & Operations

Location:
243 Consumers Road, Toronto, Ontario, M2J 4W8
At Shoppers Drug Mart, we’re innovating health and wellness in Canada. From prescriptions to walk-in clinics, and a beloved loyalty program, we’re caring and supporting our customers in new ways every day.
With more than 1,300 locally owned and operated stores from coast to coast, the Shoppers Drug Mart network is more than a great place to shop, it’s a great place to work. We’re committed to building our talented team who champion collaboration, kindness and inclusivity. Join our team, and help recognize a healthy future for your career and for all Canadians.
Why this role is important?
Position Overview
Reporting to the SVP, Pharmacy, the Director, Strategy & Operations is a strategic partner to the Pharmacy Operations & Transformation leadership team, responsible for driving strategic planning, operational excellence, business transformation, and execution of enterprise and divisional priorities.
The Director translates complex business priorities into actionable plans, executive insights, and measurable outcomes. Key accountabilities include coordinating the Multi-Year Plan (MYP), Current Year Plan (CYP), leading cross-functional initiatives, and developing high-quality Board of Directors and executive leadership materials.
The role also champions artificial intelligence (AI), automation, and digital solutions to improve productivity, streamline processes, and enhance decision-making. Success requires strong strategic thinking, executive communication, analytical capabilities, and hands-on execution.
Key ResponsibilitiesStrategic Leadership & Executive Partnership
Serve as a trusted advisor to the SVP and leadership team, providing strategic insights, business recommendations, and execution support.
Lead coordination of MYP, CYP, strategic reviews, and business planning processes.
Align cross-functional priorities, accountabilities, milestones, and measurable outcomes across Pharmacy and enterprise partners.
Anticipate business challenges, identify opportunities, and support executive decision-making.
Board & Executive Communications
Lead development of Board, Board Committee, Executive Leadership Team, and senior management presentations, briefing materials, and strategic reports.
Translate complex financial, operational, and strategic information into compelling, concise, data-driven narratives and actionable recommendations.
Manage executive reporting processes, coordinating stakeholder inputs, timelines, quality assurance, and final deliverables.
Anticipate leadership questions and ensure materials demonstrate accuracy, strategic alignment, and executive-level quality.
Strategic Initiatives & Transformation
Lead complex, cross-functional strategic initiatives and transformation programs from planning through implementation and value realization.
Establish project governance, workplans, milestones, accountabilities, risk mitigation, and performance reporting.
Facilitate executive steering committees, strategic workshops, and decision-making forums.
Drive change management, process redesign, implementation, and benefits realization across Pharmacy, Shoppers Drug Mart, and Loblaw Companies Limited.
AI, Technology & Automation
Champion responsible adoption of generative AI, automation, and emerging technologies to improve productivity, efficiency, and business performance.
Identify and implement AI-enabled solutions for research, analysis, reporting, presentations, workflow management, and executive decision support.
Partner with IT, Digital, Data & Analytics, and business teams to prioritize and deliver automation and digital transformation opportunities.
Promote AI literacy, innovation, and continuous improvement while ensuring alignment with enterprise security, privacy, and governance standards.
Operational Excellence & Business Insights
Identify opportunities to simplify, standardize, and optimize business processes, operating models, and workflows.
Lead continuous improvement initiatives delivering measurable productivity gains, operational efficiencies, and cost savings.
Develop KPIs, dashboards, business cases, and performance reporting to support strategic decisions and track results.
Conduct business analysis, scenario planning, and opportunity assessments, translating insights into actionable recommendations.
Leadership, Collaboration & Governance
Build strong relationships across Pharmacy, Shoppers Drug Mart, Loblaw, and enterprise functions, driving alignment and accountability.
Influence cross-functional teams and stakeholders to deliver shared objectives in a matrixed organization.
Coordinate executive meetings, strategic planning sessions, leadership communications, and governance forums.
Maintain confidentiality, sound judgment, and operational discipline while championing innovation and results-oriented execution.
Skills, Experience & EducationStrategic & Business Capabilities
Strong background in strategic planning, business transformation, operational excellence, and complex program execution.
Broad understanding of pharmacy operations, healthcare, retail, and enterprise business strategy.
Strong business acumen, financial literacy, analytical thinking, and structured problem-solving.
Demonstrated ability to advise senior executives, manage competing priorities, and translate strategy into execution.
Executive Communication & Leadership
Exceptional written, verbal, and presentation skills, including experience developing Board and C-suite materials.
Advanced PowerPoint capabilities, executive storytelling, and ability to synthesize complex information into clear, decision-oriented recommendations.
Strong executive presence, stakeholder management, influencing skills, and cross-functional leadership.
Excellent judgment, attention to detail, adaptability, and ability to operate effectively in a fast-paced environment.
AI, Technology & Digital Expertise
Advanced proficiency in generative AI and digital productivity tools, with demonstrated ability to improve analysis, reporting, workflows, and business outcomes.
Experience identifying and implementing automation, AI-enabled processes, and technology-driven operational improvements.
Advanced proficiency in Microsoft 365, particularly PowerPoint, Excel, Word, Teams, and SharePoint.
Experience with Microsoft Copilot, Power Automate, Power BI, or comparable platforms is highly desirable.
Understanding of responsible AI, information security, data privacy, and technology governance.
Role Requirements
5+ years of progressive experience in strategy, operations, transformation, consulting, or related leadership roles, preferably in pharmacy, healthcare, retail, or a complex corporate environment.
Undergraduate degree in business, finance, economics, healthcare administration, or a related discipline; MBA or graduate education preferred.
Proven experience supporting senior executives, developing Board-level materials, and executing enterprise strategic initiatives.
Demonstrated success leading cross-functional projects, transformation programs, process improvements, and change management.
Practical experience applying AI, digital tools, and automation to improve business productivity and operational performance.
Strong ability to facilitate strategic discussions, influence without direct authority, and balance enterprise strategy with hands-on execution.
PMP, Lean/Six Sigma, or equivalent certification is an asset.
Knowledge of Loblaw and Shoppers Drug Mart systems, processes, and performance metrics is an asset.
Why work at Shoppers Drug Mart?
Acting as consultants, supporting internal customers and the Associate-Owners, you will get experience unique to the retail industry while working for an award-winning national brand. Benefit from a purchase discount program, competitive pay and online learning through Academy.
Take ownership of your work and find more ways to care about your work, co-workers, customers and community.
How You’ll Succeed:
At Shoppers Drug Mart Inc., we seek great people to continually strengthen our culture. We believe great people model our values, are authentic, build trust and make connections.
If that sounds like you, and you are open-minded, responsive to change and up to the challenges provided in a fast-paced retail environment, apply today.
Employment Type:
Full time
Type of Role:
Regular
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