Director, Technology Infrastructure & Operations

GreenShield; Windsor; On-site; CAD 180,000 - 240,000; Full time

Job summary

GreenShield is seeking a Director, Infrastructure & Operations to lead the foundational platforms that support member and provider services. You will set the multi‑year roadmap for hybrid cloud, virtualization, storage, networks and disaster recovery, ensuring reliability and regulatory alignment in a Canadian health and insurance context.

You will lead a leadership team, drive platform modernization, observability (Dynatrace), automation, and vendor partnerships while partnering with contact

Qualifications

• 12+ years of progressive experience in infrastructure, cloud and technology operations, including 5+ years leading managers in a complex enterprise environment.
• Ownership of an enterprise infrastructure and cloud strategy with a funded multi-year roadmap.
• Proven success leading platform consolidation, cloud migration and modernization across a hybrid estate.
• Depth across hybrid cloud, on‑premises infrastructure, virtualization, storage, backup and enterprise networking.
• Accountability for enterprise uptime and 24/7 operations supporting business‑critical services.
• Experience establishing observability, automation or Site Reliability Engineering practices (e.g. Dynatrace).
• Disaster recovery, business continuity ownership and executive reporting.
• Vendor and commercial management credentials, including multi‑million‑dollar budgets.
• Regulated‑industry experience, ideally in financial services, insurance or healthcare.
• Executive‑level communication and stakeholder management skills.
• Post‑secondary degree in computer science, engineering, information technology or related discipline, or equivalent practical experience.

Responsibilities

• Own the multi‑year infrastructure and cloud strategy and investment roadmap.
• Translate business direction into platform architecture, lifecycle, capacity and financial plans.
• Establish standards governing workload placement, resilience, automation and cost efficiency.
• Lead platform rationalization, modernization of tooling and data centre footprint.
• Drive cloud migration, legacy retirement and infrastructure refresh.
• Advance infrastructure automation and Infrastructure‑as‑Code practices.
• Ensure infrastructure readiness, performance, scalability and recoverability.
• Provide end‑to‑end accountability for hybrid cloud and hosted environments.
• Lead 24/7 infrastructure operations and incident management.
• Partner with security, risk and compliance teams on controls and audits.
• Develop self‑service capabilities and regular governance.

Skills

Infrastructure leadership

Cloud strategy

Platform engineering

Vendor management

Executive communication

Education

Post-secondary degree in CS/Engineering/IT or related discipline

Tools

Dynatrace

Job description

WHO WE ARE

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

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

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

THE ROLE IN A NUTSHELL

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.

This is a strategic, leader-of-leaders position. 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 environment.

Core Accountabilities:

Infrastructure & Platform Strategy

Own the multi-year infrastructure and cloud strategy and investment roadmap. 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.

Platform Ownership

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.

Enterprise Uptime & Service Operations

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

Mature GreenShield's enterprise observability capability using tools such as Dynatrace and related tooling. 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

Own infrastructure disaster recovery and continuity capabilities with documented and tested recovery time and recovery point objectives. 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.

Leadership & Talent Development

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.

WHO WE'RE LOOKING FOR

• 12+ years of progressive experience in infrastructure, cloud and technology operations, including 5+ years leading managers in a complex enterprise environment.
• Demonstrated ownership of an enterprise infrastructure and cloud strategy with a funded multi-year roadmap, not only delivery execution.
• 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. Dynatrace)
• 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.

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 [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.