System Administrator - Workleap

Workleap, founded in 2006, is a Montreal-based tech company building simple, impactful products. Our offerings include Workleap Agent for manager effectiveness and ShareGate, a leading solution for Microsoft 365 migration and governance, trusted by over 15,000 companies globally. We seek individuals excited by challenging problems and eager to shape the future.

Your Role as System Administrator

As a System Administrator, you will be crucial in maintaining Workleap's core infrastructure, including our Azure-based systems, identity and access management, and security services. We are looking for someone who can rigorously manage our cloud infrastructure and continuously improve it through code rather than manual processes. You will collaborate closely with the IT Support and security teams and serve as the primary point of contact for complex incidents.

Your Impact

• Own our Azure infrastructure (virtual machines, backup, VPN, and policy) to ensure Workleap's systems remain reliable, secure, and available as the company expands.
• Manage Entra ID, Active Directory, Conditional Access, and Zscaler to provide seamless and appropriate access to tools for all employees.
• Oversee certificate lifecycle and patching (DigiCert, DCV, Azure Key Vault) to proactively prevent outages and security vulnerabilities.
• Develop and deploy infrastructure as code using Terraform and a Git pull request workflow, ensuring all changes are repeatable, reviewed, and traceable.
• Integrate AI tools like Claude into IT workflows to automate routine tasks and accelerate incident resolution.
• Lead infrastructure projects using Jira and Confluence to facilitate smooth integration of new tools and acquisitions within IT.

Your Team

Over the next 6 to 12 months, our team will focus on integrating new employees and technologies, enhancing and automating existing IT processes, and deploying new tools and processes. We are a team of six experts covering IT Support and Endpoint Administration, dedicated to keeping Workleap and its products operational daily.

What You'll Bring

• Experience with 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), along with comfort using Git and pull request workflows.
• Knowledge of networking, TLS certificates, logging, and monitoring.
• Ability to automate tasks using PowerShell or other scripting languages.
• Project management experience, specifically with Jira and Confluence.
• Experience with Claude and/or AI workflows.
• Excellent communication skills (spoken and written).

If most of this resonates with you, we encourage you to apply.

What the Job Comes With

• Base Salary: $80,000 - $105,000 CAD. This range reflects our Canada-wide compensation scale, with final offers adjusted for local market conditions.
• Annual bonus program.
• LTIP program, allowing you to share in Workleap's long-term growth.
• RRSP + Family health insurance + telemedicine + annual wellness budget.
• Flexible vacation policy.
• Remote work, with optional access to our Montreal office.
• In-person gatherings twice a year.
• Claude access for everyone.

What Drives Us

At Workleap, we create software that impacts how people experience work daily. We operate with speed, adapting to shifting priorities and iterating quickly. If you thrive in an intense environment and are not deterred by ambiguity, you'll fit right in. We are builders who leverage AI as a tool to accelerate progress and inform decisions, not to replace human judgment. If you seek real impact and a place where your decisions matter, this is it.

How We Hire

Our hiring process is built on transparency. Here’s what to expect:

1. An initial call with a recruiter.
2. A virtual interview with the hiring manager.
3. A take-home case study.
4. A meeting with future colleagues to discuss the case study.

The process may vary slightly depending on the role, and your recruiter will guide you through it. While we use AI to support certain steps, every hiring decision remains human.

We look forward to meeting you.

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