System Administrator

Canada - RemoteRemoteFull-time$80k2026-10-16 → 2026-11-10

Hybrid

Core

Maintain and improve Azure-based cloud infrastructure, identity management, and security services to ensure system reliability and security.

Role type

Senior System Administrator (Cloud Infrastructure & Security)

Builds

Azure virtual machines, backup systems, VPN, Entra ID policies, certificate lifecycle, and automated IT workflows.

Domain

Cloud Infrastructure (Azure), Identity & Access Management, Cybersecurity

Required skills

Azure administration, Entra ID (Azure AD), Terraform, Infrastructure as Code (IaC), PowerShell scripting, Git workflows, Networking, TLS certificates, Project management (Jira/Confluence), AI tool integration

Preferred skills

Linux administration, Microsoft 365 expertise, Zscaler experience, Claude/AI workflow automation

Technologies

Azure, Entra ID, Terraform, Git, PowerShell, Zscaler, DigiCert, Azure Key Vault, Jira, Confluence, Claude

Responsibilities

Own Azure infrastructure (VMs, backup, VPN, policy); Manage Entra ID, Active Directory, Conditional Access, and Zscaler; Handle certificate lifecycle and patching; Build and ship infrastructure as code; Integrate AI tools into IT workflows; Lead infrastructure projects in Jira and Confluence.

Seniority

Mid-to-Senior, hands-on IC

About Workleap

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: The Workleap Agent , our agentic HR platform that helps managers become better leaders, 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.