DIRECTOR - TECHNOLOGY INFRASTRUCTURE & OPERATIONS - HYBRID

Green Shield Canada (GSC); Windsor; Hybrid; CAD 140,000 - 210,000; Full time

Job summary

GreenShield is modernizing its technology ecosystem and expanding cloud adoption to deliver always-on services for members, providers, plan sponsors and employees.

The Director, Infrastructure & Operations leads the multi-year roadmap for infrastructure, cloud platforms, and service operations across a regulated Canadian healthcare and insurance environment.

Qualifications

• 12+ years of progressive experience in infrastructure, cloud and technology operations.
• 5+ years leading managers in a complex enterprise environment.
• Experience with platform consolidation, cloud migration and modernization across a hybrid estate.
• Regulated-industry experience, ideally in financial services, insurance or healthcare.

Responsibilities

• Own the multi-year infrastructure and cloud strategy and roadmap.
• Translate business direction into platform architecture, lifecycle and financial plans.
• Lead modernization of platforms, tooling, data centre footprint and duplicate tech.
• Oversee 24/7 infrastructure operations against defined targets and incidents.
• Advance observability, automation and reliability practices across the estate.
• Partner with contact centre and business operations to protect platforms and services.
• Own disaster recovery and business continuity with tested objectives.
• Maintain risk controls and OSFI-aligned infrastructure practices.
• Manage vendor relationships, sourcing, renewals and budgets.
• Lead and develop a multi-layer engineering and operations team.

Skills

Executive-level communication

Leadership of managers

Strategic thinking

Vendor & budget management

Platform modernization

Education

Post-secondary degree in computer science, engineering, IT or related

Tools

Dynatrace

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

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 ameans to earn a living. Our culture is one where everyone's voice is heard andvalued. Because that’s what it takesto create better health for all. We dare to challenge the status quo. And we’redriven by people who have challenged theirs. We believe that yourworkplace should empower you to be the best version of yourself. That’s 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 isn’t just about personalachievements, it's about making adifference together.
Here’s 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 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. Even if your experience doesn’t 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 [e-mail]. 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 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.