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, 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 teams to deliver modern cloud-native solutions.

Automation & Dev

Ops Depth: Practical experience building or managing deployment platforms utilizing Infrastructure-as-Code, CI/CD pipelines, Git

Ops,



or equivalent automation frameworks.

Education: Bachelors 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 solid assets.

Summary If you''re interested in the ''Director, Cloud & Managed Services'' role based in Toronto, we encourage you to apply online at Only qualified candidates will be contacted for the next steps.

We look forward to hearing from you! Randstad Canada is committed to fostering a workforce reflective of all peoples of Canada.

As a result, we are committed to developing and implementing strategies to increase the equity, diversity and inclusion within the workplace by examining our internal policies, practices, and systems throughout the entire lifecycle of our workforce, including its recruitment, retention and advancement for all employees.

In addition to our deep commitment to respecting human rights, we are dedicated to positive actions to affect change to ensure everyone has full participation in the workforce free from any barriers, systemic or otherwise, especially equity-seeking groups who are usually underrepresented in Canada''s workforce, including those who identify as women or non-binary/gender non-conforming; Indigenous or Aboriginal Peoples; persons with disabilities (visible or invisible) and; members of visible minorities, racialized groups and the LGBTQ2+ community.

Randstad Canada is committed to creating and maintaining an inclusive and accessible workplace for all its candidates and employees by supporting their accessibility and accommodation needs throughout the employment lifecycle.

We ask that all job applications please identify any accommodation requirements by sending an email to to ensure their ability to fully participate in the interview process.

📌 Director, Managed Services - Cloud (Toronto)
🏢 randstad canada
📍 Toronto