Job Description & How to Apply Below
As a principal departmental leader, you will oversee multidisciplinary platform engineering and cloud operations teams responsible for delivering secure, scalable, and automated deployment solutions across Managed Services, SaaS, and customer-managed environments. Operating in a remote-first capacity with occasional Toronto leadership cadences, you will partner closely with Engineering, Product, Security, and Customer Success to drive operational maturity, platform reliability, automation, and long-term client satisfaction in a high-growth health technology ecosystem.
Location:
Greater Toronto Area (GTA), ON
Work Arrangement: 100% Remote (with occasional in-person leadership/team cadences in the Toronto office)
Advantages
Executive-Level Impact:
Lead and scale cloud operations, platform engineering, and deployment automation strategies.
Modern Cloud Stack:
Direct platform maturity across Kubernetes, Infrastructure-as-Code, CI/CD pipelines, Git Ops, and observability frameworks.
Specialized Health Tech Domain:
Drive operational excellence and regulatory compliance in a modern health technology environment.
Flexible Working Model:
Enjoy the autonomy of a 100% remote role supported by occasional collaborative leadership sessions in Toronto.
Responsibilities
Lead and develop a strategic, scalable Cloud and Managed Services department supporting business growth, market competitiveness, and operational efficiency.
Define and execute strategic roadmaps for deployment automation, infrastructure automation, and platform engineering supporting Managed Services, SaaS, and customer-managed deployments.
Direct multidisciplinary teams responsible for designing, building, maintaining, and enhancing deployment pipelines, automation tooling, and platform capabilities.
Establish Dev Ops and Platform Engineering best practices, including Infrastructure-as-Code, CI/CD pipelines, configuration management, release automation, and deployment standardization.
Provide operational leadership for SaaS platforms, ensuring high availability, continuous performance, scalability, reliability, and cloud security compliance.
Ensure platforms are designed and operated in accordance with security-by-design principles, regulatory guidelines, and organizational policies.
Establish and implement IT program management frameworks, ITSM/ITIL practices, change management processes, and governance structures.
Partner with cross-functional leadership across Engineering, Product, Security, and Client Services to streamline incident resolutions, pre-sales support, RFXs, and contract management (SOWs, MSAs).
Manage strategic planning, prioritization, budget oversight, and resource allocation across cloud programs and platform initiatives.
Build and maintain trusted relationships with key enterprise clients, ensuring adherence to contractual obligations and service level agreements (SLAs).
Qualifications
Core Requirements & Executive Leadership Experience
Industry
Experience:
Proven health technology (Health Tech) industry experience with a deep understanding of healthcare cloud consumption, market dynamics, and client needs.
Director-Level Leadership:
Demonstrated track record operating at a Director level or higher, with significant experience managing, mentoring, and developing leaders in platform engineering, Dev Ops, and cloud infrastructure teams.
Cloud & Tech Management: 7+ years of senior cloud operations leadership experience delivering large-scale, complex technology projects and managed services.
ITSM & Governance: 5+ years of in-depth experience with ITSM frameworks, ITIL practices, cloud security, networking, and enterprise IT support.
Kubernetes & Cloud Engineering: 3+ years of direct experience working alongside cloud infrastructure and Kubernetes engineering…
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