DIRECTOR - STRATEGY & OPERATIONS ENABLEMENT - HYBRID

Green Shield Canada (GSC); Toronto; On-site; CAD 150,000 - 190,000; Full time

Job summary

GreenShield Canada (GSC) is seeking a Director, Strategy & Operations Enablement to shape portfolio strategy and translate it into disciplined execution. You will align Product, Experience and Health Outcomes with cross-functional partners, driving annual and quarterly planning and executive reporting.

The role requires strong strategic problem-solving, leadership of complex initiatives, and a track record in governance, budgeting, and performance tracking.

Qualifications

• Bachelor’s or Master’s degree in business, strategy, operations, economics, or related field.
• MBA or strategy consulting experience is a plus.

Responsibilities

• Formulate strategy and translate it into annual and quarterly priorities with clear accountabilities.
• Act as integrator across Product, Experience, Health Outcomes and enterprise partners; surface interdependencies and align decisions.
• Own the strategy-to-execution cadence with governance, planning, and executive reporting.
• Develop an integrated view of portfolio priorities, milestones, risks, and investment trade-offs.
• Lead market intelligence efforts and translate insights into strategic implications and roadmap decisions.
• Design operating mechanisms and governance processes adopted across the organization.

Skills

Strategic thinking

Executive communication

Cross-functional leadership

OKR design

Portfolio governance

Annual & quarterly planning

Budgeting & forecasting

Performance management

Education

Bachelor’s or Master’s in business or related field

MBA (preferred)

Job description

WHO WE ARE

GreenShieldis a proudly Canadian, national non-profit health care and insuranceorganization, driven by our mission of Better Health for All.We believe health care is aright, not a privilege, and we are committed to improving health outcomes,advancing health equity, and building a future where every Canadian can reachtheir full health and well-being potential.

Throughour unique integrated payer-provider ("payvider") model, we offerinsurance, administer benefits, and pay claims as a ‘payer’ while offeringhealth care services such as mental health, pharmacy, telemedicine, and chronicdisease management as a ‘provider’. As a non-profit social enterprise without shareholders, we reinvest our excessearnings to directly support underserved communities. Through GreenShieldCares, we positively impacted the health and well-being of over one millionCanadians between 2020 and 2025. What’s driving us now is the commitment to measurably impact an additionalthree million Canadians by 2030 – across mental health, essential medicines,and chronic disease management – through scalable initiatives that delivermeaningful change in pursuit of our mission of Better Health for All.

AtGreenShield, our culture is where purpose meets passion and performance. Our teams work as one to delivermeaningful, measurable impact for the people and communities we serve.

THEROLE IN A NUTSHELL

Base Salary: Range Exempt

Reporting to the SVP, Product, Experience and Health Outcomes, this role will play a critical role in shaping portfolio strategy, connecting priorities across teams, and translating strategic direction into disciplined execution and measurable business impact. The Director, Strategy & Operations Enablement will build and run the operating mechanisms that align Product, Customer Experience, Health Outcomes and cross-functional partners around a shared agenda.
The role is accountable for strengthening the strategy-to-execution system: annual and quarterly planning, portfolio governance, prioritization, executive reporting, performance management, competitive landscape monitoring, and operational enablement. It will ensure the team is focused on the right work, has the right forums and decision mechanisms, and can demonstrate progress against outcomes that matter to the clients and the business.
This is a high-impact, enterprise-facing role for a strategic operator who can bring structure to ambiguity, connect insight to action, and help the organization move from intent to execution with pace, transparency, and discipline.

Responsibilities:

• Work directly with the SVP and leadership team to help formulate strategy, frame strategic choices, connect insights across teams, and translate direction into annual and quarterly priorities, integrated plans, measurable outcomes, and clear accountabilities.
• Act as an integrator across Product, Experience, Health Outcomes and enterprise partners: surfacing patterns, identifying interdependencies, and helping leadership see the bigger picture behind decisions and trade-offs.
• Partner closely with Corporate Strategy to ensure Product, Experience, and Health Outcomes priorities are aligned with enterprise strategy, informed by competitive and market insights, and reflected in executive planning and decision-making forums.
• Own the strategy-to-execution cadence, including planning cycles, leadership forums, decision governance, executive updates, performance reviews, and follow-through on key actions.
• Build and maintain an integrated view of portfolio priorities, milestones, risks, dependencies, investment trade-offs, and performance against committed outcomes.
• Lead competitive landscape and market intelligence efforts across health benefits, digital health, product experience, personalization, member engagement, and adjacent sectors; convert insights into implications for strategy, roadmap choices, and differentiation.
• Establish operating mechanisms that improve decision quality, prioritization discipline, cross-functional alignment, and visibility into execution progress.
• Partner with Finance and business leaders on budget planning, forecasting, resource allocation, business cases, and value tracking to ensure investments are tied to strategic priorities and measurable impact.
• Support the definition and evolution of the operating model, including governance, roles, processes, decision rights, ways of working, and management routines across Product, Experience, and Health Outcomes.
• Drive preparation of executive-ready materials, including strategy narratives, decision papers, board and EC updates, planning documents, performance dashboards, and cross-functional communications.
• Identify opportunities to simplify, standardize, and improve core planning and operating processes, enabling teams to execute with greater speed, consistency, and accountability.
• Lead or incubate high-priority strategic initiatives that require focused orchestration, problem solving, change management, or cross-functional mobilization.

WHO WE'RE LOOKING FOR

• Bachelor’s or Master’s degree in business, strategy, operations, economics, engineering, health administration, or a related field; MBA or strategy consulting experience is an asset.
• 10+ years of experience across strategy, business operations, planning, transformation, management consulting, or a comparable role.
• Demonstrated experience supporting senior executives and leadership teams in translating strategy into operating plans, governance, performance routines, and measurable outcomes.
• Experience leading cross-functional initiatives in complex organizations, with the ability to influence without direct authority and drive alignment across product, digital, customer experience and business partners.
• Strong strategic problem-solving skills, with the ability to structure ambiguous issues, develop clear options, frame trade-offs, and recommend practical paths forward.
• Deep capability in annual and quarterly planning, portfolio governance, OKR/KPI design, executive reporting, performance management, and closed-loop follow-through.
• Strong business and financial acumen, including budget planning, forecasting, investment prioritization, business case development, and value realization.
• Experience conducting competitive, market, and customer research and translating external insights into strategic implications, opportunity areas, and leadership recommendations.
• Excellent executive communication skills, with the ability to create crisp narratives, synthesize complex information, and produce high-quality materials for senior audiences.
• Proven ability to design and embed operating mechanisms, decision forums, governance processes, and management routines that teams will adopt and sustain.
• Strong collaborator and integrator who can build trusted relationships, challenge constructively, and bring teams together around shared outcomes.
• Comfort operating in a fast-moving environment with shifting priorities, incomplete information, and high expectations for quality, pace, and follow-through.
• Outcome orientation with a practical understanding of how product, experience, and health outcomes come together to create business value.
• High standards for clarity, quality, and execution discipline; able to move seamlessly between strategic thinking and hands‑on delivery.

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!

AFew 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 [e-mail]. 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).

AI Usage - GreenShield leverages AI to help produce Job Descriptions, and ideate on interview questions. We also leverage AI for interview transcription support.