WHO WE ARE When it comes to health, we’re always looking for ways to push for better. It’s why we were founded in the first place. In 1957, our founder, pharmacist William Wilkinson, witnessed a mother sacrifice her health by forgoing her own medicine to pay for her sick daughter’s prescription. He knew there had to be a better way. So, he introduced North America’s first prepaid drug plan, and GreenShield was born as a not-for-profit with a mission to support better health for all Canadians.

We aren’t just a health and benefits company. We’re the only not-for-profit social enterprise that brings worlds of coverage and care together, all in one place.
We’re noble challengers, purposefully building a better way and we need the best people to help us create a more holistic approach that takes care of the mind and body.

Our mission is to create better health for all Canadians, and we know that starts with our employees.

THE ROLE IN A NUTSHELL

The Director, Strategy Development & Execution plays a critical enterprise leadership role as the owner of GreenShield’s enterprise strategy — accountable for defining strategic direction, setting enterprise priorities, and ensuring disciplined execution through to measurable outcomes.

This role owns GreenShield’s end‑to‑end enterprise strategy system, including strategy development, prioritization, execution governance, and performance management. The Director ensures that enterprise strategy is clear, coherent, decision‑ready, and actively managed across all Lines of Business, segments, and enabling functions.

Reporting to the VP, Strategy & Acquisitions, the Director operates with enterprise mandate and authority to set strategic standards, govern execution, and drive alignment across the organization. The role serves as the central point of accountability for how strategy is defined, translated into initiatives, governed, measured, and adjusted over time.
In close partnership with Executive leaders, the Board, Lines of Business, Finance, Corporate Development, Technology, and enabling functions, the Director ensures that enterprise strategy balances growth, impact, and operational feasibility — while maintaining a single, enterprise‑first view of priorities, trade‑offs, and outcomes.

Key Responsibilities:

Enterprise Strategy Ownership & Development

• Own the enterprise strategy cycle, including annual and mid‑year refreshes, market and competitive analysis, articulation of enterprise strategic themes, and definition of enterprise priorities.
• Set the enterprise strategy framework, standards, and methodologies used across the organization to ensure consistency, comparability, and strategic integrity.
• Lead the definition of “where to play / how to win” choices at the enterprise level, ensuring clear strategic intent across Lines of Business and segments.
• Partner with Line of Business and segment leaders to co‑develop strategies and capability roadmaps, while retaining ownership of enterprise alignment, coherence, and prioritization decisions.
• Own and govern the build / buy / partner decision framework for major growth, capability, and investment decisions, bringing clear enterprise recommendations into Executive and Board forums.
• Ensure social impact, emerging technology, and AI considerations are embedded into enterprise strategy, prioritization, and success measures in partnership with GS Cares and functional leaders.
• Own the enterprise strategy narrative and materials for Executive Committee and Board Strategy sessions, ensuring a clear link between context, choices, investments, and outcomes.

Strategy Execution, Portfolio & Performance Governance

• Own and operate GreenShield’s enterprise strategy execution system, including governance forums, operating rhythm, standards, templates, and performance disciplines.
• Set and govern the enterprise strategic initiative intake, prioritization, and portfolio, maintaining a single enterprise roadmap aligned to strategic themes and value logic.
• Establish and govern enterprise success measures, including the enterprise strategy scorecard, OKRs, and dashboards, integrating financial, customer, operational, and social impact outcomes.
• Lead Line of Business and segment Strategy Execution Reviews (QBRs) and the Enterprise Strategy & Performance
• Review, exercising authority to drive reprioritization, trade‑offs, and course correction.
• Own exception management, including identification of at‑risk initiatives, execution risk management, and approval of re‑baselining decisions where justified.
• Ensure acquisitions, partnerships, and major integrations are embedded into the enterprise strategy portfolio and performance framework, in partnership with Corporate Development and Lines of Business.
• Produce concise, decision‑oriented strategy execution reporting for Executive Committee and the Board.

Enterprise Leadership & Authority

• Act as the enterprise owner and steward of strategy, providing clear direction, guardrails, and governance across the organization.

• Serve as a trusted advisor to Executive and senior leaders on strategic choices, trade‑offs, and enterprise prioritization.

• Represent enterprise strategy ownership in senior leadership forums, transformation discussions, and governance bodies.

• Drive enterprise‑first thinking, alignment, and accountability across a complex, matrixed organization

WHO WE'RE LOOKING FOR

Experience

• 6–10+ years of progressive experience in enterprise strategy development, execution, transformation, or related leadership roles.

• Demonstrated experience owning and governing enterprise strategy, including portfolio management and performance oversight.

• Proven ability to operate with enterprise authority and influence Executive and senior leaders in complex environments.
  Education

• Post‑secondary degree in Business, Economics, Engineering, or a related field.

• MBA or equivalent advanced degree considered an asset.

Knowledge & Skills

• Deep understanding of enterprise strategy, operating models, and execution governance.
• Strong ability to translate strategy into enterprise priorities, execution plans, and measurable outcomes.
• Exceptional analytical, problem‑solving, and decision‑making skills.
• Executive‑level written and verbal communication skills, including Board‑ready materials.
  Abilities
• Confident, credible leadership presence with the ability to set direction and drive enterprise alignment.
• Highly organized, disciplined, and comfortable managing competing enterprise priorities.
• Collaborative yet decisive leadership style, grounded in enterprise‑first thinking.
• Comfortable leading through ambiguity, change, and complex trade‑offs.

THE CULTURE We believe a career should be meaningful. Not just a means to earn a living. Our culture is one where everyone's voice is heard and valued. Because that’s what it takes to create better health for all. We dare to challenge the status quo. And we’re driven by people who have challenged theirs. We believe that your workplace should empower you to be the best version of yourself. That’s why we provide a place where you can be inspired, challenged, and rewarded.

Where your growth means our growth.
Where your voice is heard and valued.
Where your work has purpose. And purpose matters.

We believe our people are critical to our overall success. Inclusivity makes us a stronger, smarter and more informed organization. Being intentionally inclusive of diverse backgrounds, perspectives and experiences will enhance our company culture to positively impact how we support our communities. A career at GreenShield isn’t just about personal achievements, it's about making a difference together.

Here’s to Better Health for All!

A FEW MORE DETAILS Proficiency in English is required for this position. As part of this role, you will be required to communicate with colleagues or customers who use English as their primary language. By requiring English proficiency for this position, we aim to ensure that our employees can excel in their roles, collaborate, and communicate effectively, and contribute to the success of our organization.

GS supports diversity, equity and inclusion in our teams and communities, and we value the unique contributions made by all. Even if your experience doesn’t align perfectly to every requirement, we invite you to apply. We encourage applications from all candidates and will accommodate needs under human rights legislation throughout all stages of the recruitment and selection process. Please let us know of any accommodation through requestforaccommodation@greenshield.ca. Information received relating to accommodation will be addressed confidentially.

Providing this information gives GS consent to use your personal information to assess your suitability for specific positions, future opportunities or for your personnel file. Your résumé will be held in strict confidence and will be viewed only by the Organization. Information may be stored outside of Canada and could be used for aggregate statistical purposes (which uses no personal identification).