Director - Technology Infrastructure & Operations - Hybrid

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.