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Director Strategy & Operations Enablement Hybrid

GreenShield


Job Location:

Toronto - Canada

Monthly Salary: Not provided by the employer
Posted: 19 September 2026 (2 hours ago)
Application Deadline: 17 December 2026
Vacancies: 1 Vacancy

Job Summary

WHO WE ARE

GreenShieldis a proudly Canadian national non-profit health care and insuranceorganization driven by our mission of Better Health for believe health care is aright not a privilege and we are committed to improving health outcomesadvancing 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. Whats driving us now is the commitment to measurably impact an additionalthree million Canadians by 2030 across mental health essential medicinesand 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 WERE LOOKING FOR

  • Bachelors or Masters 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 ameans to earn a living. Our culture is one where everyones voice is heard andvalued. Because thats what it takesto create better health for all. We dare to challenge the status quo. And weredriven by people who have challenged theirs. We believe that yourworkplace should empower you to be the best version of yourself. Thats why we provide aplace 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 arecritical to our overall success. Inclusivity makes us a stronger smarter andmore informed organization. Being intentionally inclusive of diversebackgrounds perspectives and experiences will enhance our company culture topositively impact how we support our communities. A career at GreenShield isnt just about personalachievements its about making adifference together.

Heres to Better Health for All!

AFEW MORE DETAILS
Proficiency in English is requiredfor this position. As part of this role you will be required to communicatewith colleagues or customers who use English as their primary language. By requiring English proficiency for thisposition we aim to ensure that our employees can excel in their rolescollaborate and communicate effectively and contribute to the success of ourorganization.

GS supports diversity equity andinclusion in our teams and communities and we value the unique contributionsmade by all. Even if your experience doesnt align perfectly to everyrequirement we invite you to apply. We encourage applications fromall candidates and will accommodate needs under human rights legislationthroughout all stages of the recruitment and selection process. Please let usknow of any accommodation through Information received relating toaccommodation will be addressed confidentially.

Providing this information givesGS consent to use your personal information to assess your suitability forspecific positions future opportunities or for your personnel file. Yourrésumé will be held in strict confidence and will be viewed only by theOrganization. Information may be stored outside of Canada and could be used foraggregate 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.


Required Experience:

Director