Workleap is a Montreal-based tech company, founded in 2006. 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. 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.

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. You'll work closely with the IT Support and security teams, and you'll be the go-to person when an incident gets complex.

Own our Azure infrastructure (virtual machines, backup, VPN and policy) to keep Workleap's systems reliable, secure and available as the company grows.

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.

Over the next 6 to 12 months, the team will help integrate recent employees and technologies, improve and automate existing IT processes, and deploy current 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.

Windows Server and Linux administration in Azure-based environments;

Strong knowledge of Microsoft 365, Entra ID (Azure AD) and Azure;

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;

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.

Work from home, with access to our Montreal office.

At Workleap, we build software that sits at the center of how people experience work, every day, at every level.

Priorities shift, decisions get made with the information we have, and we iterate. If you thrive on intensity and ambiguity doesn't slow you down, you'll feel right at home. AI is part of our toolkit. Here's how it works: a first call with a recruiter, then a virtual interview with the hiring manager. We use AI to support certain steps of the process, but every hiring decision remains human.

LI-Remote

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📌 IT System Administrator (Fully Remote) (Montreal)
🏢 Pingboard
📍 Montreal