workleap · Montréal, Quebec, Canada
Company Description Workleap is a Montreal-based tech company, founded in 2006. We're builders at heart, we make simple products that actually matter to the people who use them. We have two product lines: Workleap Agent , our newest solution built to make every manager more effective, and ShareGate , the world's leading solution for Microsoft 365 migration and governance. More than 15,000 companies worldwide trust us to do exactly that. We're intentional about who joins us. If you're the kind of person who gets excited by a hard problem and wants to help shape what comes next, there's a place for you here. 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…
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