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Added 41 mins ago
Director, Customer Technology - Digital Technology Solutions
Hydro One Networks Inc
Toronto, ON
The Director, Customer Experience – DTS is accountable for the end-to-end technology experience supporting Hydro One’s customers, spanning digital channels, billing, CRM, integrations,…
Added 56 mins ago
IMIT Provincial Manager - Registration & Switchboard Services
Nova Scotia Health Authority
Truro, NS
Full-time
The IMIT Provincial Manager, Registration and Switchboard Services reports to the IMIT Director Registration, Scheduling and Switchboard and is responsible for the transformation of health…
Added 56 mins ago
Sr. Client Success Services Program Manager
Open Text Corporation
Waterloo, ON
…and contribute to projects that shape the future of digital…
Added 56 mins ago
Sr. Client Success Services Program Manager
Open Text Corporation
Waterloo, ON
…and contribute to projects that shape the future of digital…
Added 1 hour ago
Sr. Client Success Services Program Manager
OpenText
Waterloo, ON
Full-time
…and contribute to projects that shape the future of digital…
Added 2 hours ago
Director, RBC Bank Fraud Strategy
Royal Bank of Canada
Toronto, ON
Full-time
Be the trusted advisor to business partners and assess current and emerging fraud risks to develop and implement strategic plans that support business transformation.
Added 3 hours ago
IT Senior Project Manager (SAP/Business Transformation specialization)
Saputo Inc.
Bas-Saint-Laurent, QC
Full-time
Saputo is looking for an IT Senior Project Manager (SAP / Business Transformation specialization) to join our IT PMO team. This is an exciting opportunity to be part of a dynamic global…
Added 3 hours ago
IT Project Manager (Infrastructure / Cybersecurity specialization)
Saputo Inc.
Bas-Saint-Laurent, QC
Full-time
…translating ambiguous business objectives into a clear delivery strategy, work breakdown structure, staffing model, deliverables, and integrated project plan. You are responsible for…
Added 3 hours ago
Senior Director- Budgeting, Sustainability and Data Quality
Canadian College of Health Leaders - Northwestern Ontario Chapter
St. John's, NL · Greater St. John's Metropolitan Area
Full-time
NL Health Services is seeking a strategic and collaborative leader to serve as Senior Director, Provincial Budgeting, Sustainability and Data Quality.
Added 3 hours ago
Gestionnaire principal TI, Architecture d’entreprise
Saputo Inc.
Bas-Saint-Laurent, QC
Full-time
…Saputo’s global operations. This role works closely with the Sr. Director and is responsible for defining and governing the enterprise-wide technology architecture strategy to ensure…
Added 3 hours ago
Gestionnaire principal TI, Architecture d’entreprise
Saputo Inc.
Georgetown, ON
Full-time
…Saputo’s global operations. This role works closely with the Sr. Director and is responsible for defining and governing the enterprise-wide technology architecture strategy to ensure…
Added 3 hours ago
Internal Communications Advisor
College of LPN and HCA of Alberta (CLHA)
Edmonton, AB
Full-time
Reporting to the Director of Communications, the Internal Communications Advisor plays a key role in helping employees understand and connect with the CLHA’s mandate, strategic priorities,…
Added 3 hours ago
Financial Analyst (Consolidation)
Husky Technologies
Bolton, ON
Full-time
…talent to develop with us as we pursue our ambitious growth…
Added 3 hours ago
Manager AI and Digital Innovation Job Details | Richmond Hill
City of Richmond Hill
Richmond Hill, ON
Full-time
Reporting to the Director Information Technology/CIO, the Manager, AI and Digital Innovation is the City’s catalyst for turning emerging technologies into practical, measurable…
Added 3 hours ago
Director, Procurement Strategy & Transformation
Manulife
Toronto, ON
Full-time
As Director, Strategy & Transformation, you will partner closely with Procurement and Administrative Services leadership to shape and execute strategic priorities that drive meaningful…
Added 4 hours ago
IT Senior Project Manager (SAP/Business Transformation specialization)
Saputo Inc.
Montreal, QC · Saint-Laurent, QC
Full-time
Saputo is looking for an IT Senior Project Manager (SAP / Business Transformation specialization) to join our IT PMO team. This is an exciting opportunity to be part of a dynamic global…
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IT Senior Project Manager (SAP/Business Transformation specialization)
Saputo Inc.
Georgetown, ON
Full-time
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Added 4 hours ago
IT Project Manager (Digital / AI specialization)
Saputo Inc.
Montreal, QC · Saint-Laurent, QC
Full-time
…deployments, process automation, data-driven solutions, and business transformation initiatives across our global divisions. Your ability to communicate with and collaborate IT and business…
Added 4 hours ago
Executive Director Human Resources Business Partnerships
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Saskatoon, SK
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Department: Executive Director - HR Business Partnerships
Added 4 hours ago
Director Transformation - Global Real Estate & Corporate Services (18-month Contract)
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Toronto, ON
Reporting to the VP, Strategy and BRM, the Director, Transformation is accountable for leading the end-to-end delivery of GRECS’ global outsourcing transformation, ensuring the program…
Added 4 hours ago
Director, Medical Assistance in Dying (MAID)
Government of Alberta
AB
Job Title: Director, Medical Assistance in Dying (MAID)
Added 4 hours ago
Sr. Director, Evergreen Subscription Sales- Americas
Everpure
ON · Ontario, Canada
Full-time
The Americas Senior Director, Evergreen Subscription Sales, leads the segment strategy, vision, and execution of the Evergreen subscription portfolio for the Americas Core segment. This…
Added 4 hours ago
IT Project Manager (Digital / AI specialization)
Saputo Inc.
Georgetown, ON
Full-time
…deployments, process automation, data-driven solutions, and business transformation initiatives across our global divisions. Your ability to communicate with and collaborate IT and business…
Added 4 hours ago
Senior Director, AI Research- FR
RBC
Montreal, QC
Full-time
RBC's AI Group is building the future of AI-powered banking, and our research teams are at the forefront of this transformation. Reporting to the VP, Applied AI Research & Solutions, the…
Added 4 hours ago
Marketing Engineer & Director of AEO
Equiniti
Toronto, ON
Full-time
We are looking for a Marketing Engineer & Director of AEO to own how our brand is discovered, understood, cited, and recommended across search engines, answer engines, AI assistants, and…

Green Shield Canada

DIRECTOR - TECHNOLOGY INFRASTRUCTURE & OPERATIONS - HYBRID

Windsor, ON, Canada

Experience: 12+ years of progressive experience in infrastructure, cloud and technology operations, including 5+ years leading managers in a complex enterprise environment.
Posting language: English
Posted: Sep 21, 2026

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Original 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

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 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 [email protected]. 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.

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More about this job

Responsibilities

The Director is responsible for the strategic leadership of infrastructure engineering, cloud platforms, and enterprise operations to ensure resilient and scalable technology services. They will oversee multi-year roadmaps, platform modernization, and 24/7 service operations while managing vendor ecosystems and operational risk.

Requirements

Candidates must have over 12 years of progressive experience in infrastructure and cloud operations, including at least 5 years in a leadership role. A post-secondary degree in computer science, engineering, or a related field is required, along with proven success in managing complex hybrid environments and enterprise-level transformations.

Skills

Infrastructure Strategy
Cloud Platforms
Enterprise Networking
Database Services
Service Operations
Site Reliability Engineering
Disaster Recovery
Observability
Infrastructure Automation
Vendor Management
Budget Management
Team Leadership
Risk Management
Operational Resilience
Stakeholder Management

Visa sponsorship

Not detected in the job text

Keywords

Infrastructure
Cloud
Hybrid Cloud
Enterprise Networking
Database Services
Site Reliability Engineering
Observability
Dynatrace
Disaster Recovery
Business Continuity
Infrastructure-as-Code
Automation
Vendor Management
Budgeting
Risk Management
Compliance
OSFI
Leadership
Platform Engineering
Modernization
Telephony
Virtualization
Windows Server
Oracle
Google Cloud
Microsoft
Managed Services
Strategic Planning
Operational Resilience
Technology Transformation

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