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. 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.

GreenShield is continuing the modernization of its technology ecosystem while operating always-on services for members, providers, plan sponsors and employees. As GreenShield expands cloud adoption, enables AI-driven technologies and advances enterprise transformation through infrastructure, contact centre and service transformation initiatives, resilient and scalable technology platforms are essential to business performance and customer experience.

The Director, Infrastructure & Operations is accountable for the foundational platforms that support GreenShield's business and customer-facing services. The role provides strategic leadership for infrastructure engineering, cloud platforms, enterprise networking, database services, service operations, reliability, disaster recovery and observability.

The Director sets and executes a multi-year roadmap, leads platform consolidation and modernization, governs a complex vendor ecosystem, and is accountable for enterprise availability and operational resilience within a regulated Canadian healthcare and insurance workplace.

Translate GreenShield's business direction into platform architecture, lifecycle, capacity and financial plans. Establish standards that govern workload placement, technology currency, resilience, automation and cost efficiency across the hybrid estate.

Enterprise Modernization & Transformation Lead the rationalization and modernization of platforms, tooling, data centre footprint and duplicate technologies. Drive cloud migration, legacy retirement and infrastructure refresh with measurable reductions in technical debt, operational risk and complexity.

Advance infrastructure automation, Infrastructure-as-Code and repeatable engineering practices.

Enable transformation programs by ensuring infrastructure readiness, performance, scalability and recoverability.





Develop platform engineering and self-service capabilities where they improve speed, control and consistency.

Provide end-to-end accountability for GreenShield's infrastructure estate, including hybrid cloud and hosted environments, Windows Server and virtualization, storage and backup, enterprise networking and telecommunications, and database platforms i.e. Oracle, Google, and Microsoft and others. Ensure platforms meet defined availability, performance, capacity, security and recoverability targets.

Lead 24/7 infrastructure operations against defined service and performance targets. Own major incident command, problem management, operational reviews and infrastructure change governance. Establish clear service ownership, operational measures and continuous-improvement disciplines that protect business-critical services.

Observability, Automation & Reliability Move the organization from reactive alerting toward proactive detection, service health intelligence, automated remediation and prevention. Introduce practical Site Reliability Engineering practices that reduce operational toil and improve reliability.

Contact Centre & Business Partnership Partner directly with contact centre and business operations leaders to protect the platforms, telephony, integrations and network paths on which member and provider servicing depends. Align capacity, maintenance windows, release activity and recovery priorities to business volume cycles. Treat customer-facing availability as a first-order service commitment.

Business Continuity & Operational Resilience Lead recovery exercises with business and technology stakeholders, close resilience gaps and provide transparent reporting on readiness and risk. Partner with Information Security on controls, audits and remediation. Security remains a separate function, while this role is accountable for implementing and sustaining infrastructure controls.

Risk, Compliance & Technology Currency Maintain infrastructure practices that support applicable OSFI obligations and GreenShield's internal risk requirements. Establish disciplined lifecycle and end-of-life management across the estate, maintain evidence of control effectiveness and ensure remediation commitments are completed with urgency and accountability.

Vendor, Commercial & Financial Management Own a broad portfolio of cloud, infrastructure, database, telecom, monitoring and managed-service partners. Set sourcing and consolidation strategy, lead negotiations and renewals, govern performance against contractual commitments, and manage infrastructure budgets, licensing and consumption. Improve value through disciplined demand management, commercial leverage and accountable partnerships.





Lead and develop a multi-layer organization of managers and technical specialists. Build succession depth, raise engineering and operational standards, clarify accountability, and foster a service-oriented culture grounded in collaboration, automation, continuous learning and measurable business outcomes.

12+ years of progressive experience in infrastructure, cloud and technology operations, including 5+ years leading managers in a complex enterprise environment.

Proven success leading platform consolidation, cloud migration, legacy retirement and modernization across a hybrid estate.

Depth across hybrid cloud, on-premises infrastructure, virtualization, storage, backup and enterprise networking connecting on-premises, hosted and cloud environments.

Accountability for enterprise uptime and 24/7 operations supporting business-critical and high-volume customer-facing services.

Experience establishing modern observability, automation or Site Reliability Engineering practices (i.e. Demonstrated ownership of disaster recovery and business continuity, including recovery objectives, exercise design, remediation and executive reporting.

Strong vendor and commercial management credentials, including sourcing, negotiation, managed-service governance and multi-million-dollar budget accountability.

Regulated-industry experience, ideally in financial services, insurance or healthcare, with familiarity with technology risk, privacy and operational-resilience expectations.

Executive-level communication and stakeholder-management skills, with the ability to translate technical complexity into business risk, investment choices and measurable outcomes.

Post-secondary degree in computer science, engineering, information technology or a related discipline, or equivalent practical experience.

Being intentionally inclusive of diversebackgrounds, perspectives and experiences will enhance our company culture topositively impact how we support our communities. 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 roles,collaborate, 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. We encourage applications fromall candidates and will accommodate needs under human rights legislationthroughout all stages of the recruitment and selection process. Providing this information givesGS consent to use your personal information to assess your suitability forspecific positions, future opportunities or for your personnel file.

Information may be stored outsideof 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. #

📌 Director - Technology Infrastructure & Operations - Hybrid (Windsor)
🏢 Green Shield Canada (GSC)
📍 Windsor