Senior Systems Engineer (Hybrid, Toronto, Vancouver, Montreal)

What We’re Looking For

We are seeking a Senior Systems Engineer to own and evolve our modern, cloud-first technology environment. This is a high-impact, hands-on role for someone who operates with strong judgment, moves quickly, and takes a proactive approach to security, automation, and reliability.

You’re the right fit for this role if you:

• Take ownership and operate confidently as the go-to systems expert
• Proactively identify risks, inefficiencies, and improvements—and act on them
• Apply strong judgment to security, identity, and system design decisions
• Prioritize automation and scalable solutions over manual processes
• Thrive in fast-paced environments where you can make tangible impact quickly

What You'll Do

Own and administer our Microsoft 365 environment, including Azure, Entra ID, Intune, Exchange, SharePoint, and Teams.

Manage Windows and macOS endpoints using modern, cloud-based management and monitoring practices.

Ensure high reliability, consistent configuration, and strong operational performance across all devices.

Lead identity and access management, including MFA and conditional access policies.

Strengthen and maintain security controls aligned to compliance and audit requirements.

Proactively identify, assess, and remediate risks, vulnerabilities, and configuration drift.

Align security controls and practices to recognized industry frameworks such as NIST, CIS benchmarks, ISO 27001, or SOC 2, ensuring audit readiness and continuous compliance improvement.

Manage the lifecycle of SaaS applications, including provisioning, access controls, and license optimization.

Partner with internal teams to onboard and offboard tools securely and efficiently.

Develop and maintain PowerShell scripts for administration, reporting, and workflow automation.

Reduce manual effort through thoughtful automation and continuous process improvement.

Lead key IT initiatives including office builds, migrations, tooling rollouts, and security enhancements.

Drive projects end-to-end—from planning and execution through documentation and operational handoff.

Serve as a senior escalation point for complex technical issues while supporting broader IT operations as needed.

Conduct root-cause analysis and ensure timely, high-quality resolution.

Operate effectively within ITSM platforms (Freshservice, Jira, HaloITSM, or similar).

Collaborate with IT leadership on architecture decisions, roadmap planning, and vendor management.

Identify opportunities to improve systems, processes, and standards across the organization.

Partner with management to help conduct Vendor Risk Assessments for new vendors.

Own intake, prioritization, sequencing, and capacity planning across initiatives.

What You Bring

• 8–12+ years of experience
• Strong experience administering Microsoft 365 in a modern, cloud-first environment
• Deep expertise in identity management, endpoint management, and security best practices
• Proven PowerShell scripting experience
• Experience supporting Windows and macOS environments at scale
• Familiarity with ITSM/ticketing platforms (Freshservice, Jira, HaloITSM, or similar)
• A proactive, solutions-oriented mindset with the ability to operate independently and drive initiatives forward