Director, Strategy & Operations

Loblaw Companies Limited; Toronto; On-site; CAD 128,000 - 176,000; Full time

Benefits offered by this job

Purchase discount program

Job summary

Shoppers Drug Mart Inc. seeks a Director of Strategy & Operations to drive strategic planning, transformation, and executive partnerships. This role champions AI and digital solutions to improve productivity and decision-making across Pharmacy and Loblaw enterprises.

You will coordinate cross-functional initiatives, develop executive materials, and lead governance forums, delivering measurable outcomes and strategic alignment.

Qualifications

• Strong background in strategic planning, transformation, and execution.
• Experience advising senior executives and translating strategy into action.
• Knowledge of pharmacy/healthcare and retail enterprise strategies.

Responsibilities

• Serve as trusted advisor to SVP and leadership, guiding strategic insights and execution.
• Lead coordination of multi-year and yearly plans and performance reporting.
• Drive cross-functional transformation programs from planning to value realization.
• Champion AI, automation, and digital solutions to improve productivity and decision-making.
• Develop board materials, executive reporting, and governance artifacts.

Skills

Strategic planning

Business transformation

Operational excellence

Cross-functional leadership

Executive communication

Education

Undergraduate degree in business/finance/economics/healthcare administration

MBA or graduate education preferred

Tools

Microsoft 365

PowerPoint

Power BI

AI tools

Job description

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?

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 Responsibilities

Strategic 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 & Education

Strategic & 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.

Employment Type

Full time

Type Of Role

Regular

Shoppers Drug Mart Inc. recognizes Canada’s diversity as a source of national pride and strength. We have made it a priority to reflect our nation’s evolving diversity in the products we sell, the people we hire, and the culture we create in our organization. Accommodation is available upon request for applicants with disabilities in the recruitment and assessment process and when hired.

In addition, we believe that compliance with laws is about doing the right thing. Upholding the law is part of our Code of Conduct – it reinforces what our customers and stakeholders expect of us.

Hiring Range / Échelle Salariale à L’embauche

$128,000.00 - $176,000.00 / 128.000,00$ - 176.000,00$ (per year / par an)

A candidate’s experience and knowledge as well as the geographical region in which the position is located may be factored into the pay a candidate receives for this position. This posting is for an existing vacancy. The Company uses artificial intelligence for the purpose of screening, assessing and/or selecting applicants for this position. / L’expérience et les connaissances d’un candidat ainsi que la région géographique dans laquelle le poste est situé peuvent être prises en compte dans la rémunération qu’un candidat reçoit pour ce poste. Cette offre d’emploi concerne un poste vacant existant. L’entreprise utilise l’intelligence artificielle dans le but de filtrer, d’évaluer et/ou de sélectionner les candidats à ce poste.

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