Director Cloud Managed Services

We are seeking a highly accomplished Director, Cloud & Managed Services for an enterprise-level leadership opportunity based in the Greater Toronto Area. In this role, you will take on a premier executive capacity, leading the strategic development, operational excellence, and evolution of cloud platforms, deployment automation, and managed services capabilities to support cloud-native growth. 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, GitOps, and observability frameworks. - Specialized HealthTech 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 DevOps 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 (HealthTech) 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, DevOps, 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 teams to deliver modern cloud-native solutions. - Automation & DevOps Depth: Practical experience building or managing deployment platforms utilizing Infrastructure-as-Code, CI/CD pipelines, GitOps, or equivalent automation frameworks. - Education: Bachelor’s degree in Computer Science, Information Technology, Business Administration, or a related field (or equivalent work experience). Preferred Assets & Certifications - Security & Observability Compliance: Experience ensuring organizational alignment with security frameworks such as HITRUST, ISO 27001/27017/27018, SOC-2, and managing enterprise logging/tracing observability platforms. - Financial & Commercial Acumen: Experience managing cloud budgets, cloud pricing models, SOW negotiations, and pre-sales architecture consultations. - Professional Certifications: Relevant certifications such as CISM, CCSP, CISSP, ITIL, or TOGAF are considered strong assets.