System Administrator

Workleap Inc.; United States; Hybrid; USD 80,000 - 105,000; Full time

Benefits offered by this job

Annual bonus program

LTIP program

RRSP + health insurance + telemedicine

Flexible vacation policy

Remote work with Montreal office

Job summary

Workleap Inc. in Montreal seeks a System Administrator to own the Azure-based infrastructure, identities, access controls, and security services that connect our employees to the tools they use daily.

You will automate deployments with Terraform, manage Entra ID, AD, and patching, and collaborate with IT Support and security teams to resolve incidents efficiently while adopting new AI workflows like Claude.

Qualifications

• 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), 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).

Responsibilities

• 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.

Skills

Windows Server

Linux admin

Microsoft 365

Entra ID

Git workflows

PowerShell

Terraform

Jira

Confluence

Claude AI

Networking

TLS certificates

Monitoring

Communication

Tools

Terraform

Git

Jira

Confluence

Job description

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, andShareGate, 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 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?

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.

What drives us

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

We move fast. 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.
We’re builders. We do what it takes to move forward. AI is part of our toolkit. We use it to go faster and decide smarter, not to replace judgment.

If you want real impact and a place where your decisions matter, this is it.

How we hire

Transparency is how we hire — for you as much as for us.

Here’s how it works: a first call with a recruiter, then a virtual interview with the hiring manager. You’ll then complete a take-home case study, followed by a meet with future colleagues to discuss it together. Depending on the role, the process may vary slightly — your recruiter will walk you through it on your first call.

We use AI to support certain steps of the process, but every hiring decision remains human.

We can’t wait to meet you.

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