System Administrator

Your role

As a System Administrator, you'll keep the foundation of Workleap running: our Azure-based infrastructure, the identities and access that connect everyone to their tools, and the security services that protect them. Our infrastructure now lives in the cloud, and we need someone who can run it with rigor and keep improving it through code rather than manual work. You'll work closely with the IT Support and security teams, and you'll be the go-to person when an incident gets complex.

Your impact: 

• Own our Azure infrastructure (virtual machines, backup, VPN and policy) to keep Workleap's systems reliable, secure and available as the company grows.
• Run Entra ID, Active Directory, Conditional Access and Zscaler so that every employee gets the right access to the right tools, without friction.
• Own the certificate lifecycle and patching (DigiCert, DCV, Azure Key Vault) to prevent outages and security gaps before they reach our teams.
• Build and ship infrastructure as code with Terraform and a Git pull request workflow, so that every change is repeatable, reviewed and traceable.
• Integrate AI tools such as Claude into IT workflows to automate recurring tasks and speed up incident resolution.
• Lead infrastructure projects in Jira and Confluence to help IT absorb new tools and acquisitions smoothly.

Your team

Over the next 6 to 12 months, the team will help integrate new employees and technologies, improve and automate existing IT processes, and deploy new tools and processes. We're a team of six experts working across disciplines such as IT Support and Endpoint Administration, and we keep Workleap and its products running every day.

What you'll bring

• Windows Server and Linux administration in Azure-based environments;
• Strong knowledge of Microsoft 365, Entra ID (Azure AD) and Azure;
• Proficiency with Terraform and infrastructure as code (required), and comfort with Git and pull request workflows;
• Knowledge of networking, TLS certificates, logging and monitoring;
• Ability to automate with PowerShell or other scripting languages;
• Project management experience, with Jira and Confluence;
• Experience with Claude and/or AI workflows;
• Excellent communication skills (spoken and written).

Most of this sounds like you? Apply.

What the job comes with

• Base salary: $80 000 - $105 000. This range reflects our Canada-wide compensation scale. Final offers may be adjusted based on the candidate's region to align with local market conditions.
• Annual bonus program.
• LTIP program, share in Workleap's long-term growth.
• RRSP + Family health insurance + telemedicine + annual wellness budget.
• Flexible vacation policy.
• Remote work, with access to our Montreal office.
• In-person gatherings twice a year.
• Claude access, for everyone.