---
title: 'System Administrator at Workleap - en'
canonical: 'https://feeny.ai/job/system-administrator-workleap-en-montreal-edzsmrsyyzjz'
type: 'job'
last_seen: '2026-10-19'
---

# System Administrator at Workleap - en

- **Company:** Workleap - en
- **Location:** Montréal, Canada
- **Work type:** remote
- **Posted:** 2026-10-16
- **Last confirmed live:** 2026-10-19
- **Apply:** https://job-boards.greenhouse.io/workleap/jobs/5264689007

## 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](https://workleap.com/), our newest solution built to make every manager more effective, and [ShareGate](https://sharegate.com/), 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? Apply.

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.

By applying, you confirm that you have read and agree to our [privacy policy](https://workleap.com/trust-center/privacy).

#LI-Remote

## About Workleap - en

## Company Overview
- **One-liner**: Workleap is an AI-powered talent management platform that brings engagement, performance, and compensation into one connected system for small to mid-sized businesses.
- **Entity Type**: Private (Growth stage, series not publicly disclosed)
- **Headquarters**: Montreal, Quebec, Canada
- **Founded**: 2006
- **Founders**: Simon De Baene, Guillaume Roy, Sébastien Leduc

## Core Business
- **Primary Industry**: Human Resources Technology (HR Tech), Employee Experience, Talent Management
- **Target Customers**: SMBs and growing businesses with small or generalist HR teams (B2B)
- **Mission**: "To make work simpler" and help HR leaders ignite employee potential and boost business results.

## Products & Services
- **[Workleap Platform](https://workleap.com/)**: An AI-powered HR suite that includes employee engagement surveys (Officevibe), performance reviews (Performance), and compensation management (Compensation). Designed as a unified system to replace fragmented HR tools.
- **[ShareGate](https://workleap.com/)**: A Microsoft 365 migration and governance solution for IT professionals, focused on simplicity and security. Operates as a separate product line under the Workleap umbrella.

## Market Standing
- **Valuation**: Not publicly disclosed.
- **Key Metrics**: 70,000+ leaders worldwide use Workleap; 20,000+ companies across the entire customer base; 375+ employees.
- **Notable Investors/Partners**: Not specifically listed. Investors are not publicly disclosed.
- **Growth Signals**: Significant customer growth (from "over 70,000 leaders" on the about page), investment in AI features (manager agent, survey summaries), and expansion of the ShareGate product line. The company has a remote-first talent model, hiring across Canada.

## Competitive Advantages
- **Purpose-built for Small HR Teams**: Workleap is designed specifically for smaller or generalist HR teams that lack the resources of enterprise HR departments, offering simple, high-adoption tools.
- **Unified AI Platform**: Combines engagement, performance, and compensation in one system, reducing the "DIY chaos" and clunky legacy tools common in HR tech.
- **High User Satisfaction**: Praised on G2 for fast implementation, ease of use, and high adoption rates.
- **Strong Market Position in M365 Ecosystem**: ShareGate is a leading tool for Microsoft 365 migration and governance, providing a strong, separate revenue stream and brand recognition among IT professionals.

## Strategic Focus
- **AI-First Management Agent**: Developing a proactive "manager agent" that drafts 1:1 agendas, surfaces signals, and helps drive performance reviews, making great management a repeatable process.
- **Product Expansion**: Continuing to unify engagement, performance, and compensation into a single, intelligent platform.
- **Remote-First Culture**: Committed to a remote-first policy (work from anywhere in Canada, up to 150 days abroad annually) with twice-yearly in-person gatherings, aiming to attract top talent without geographic constraints.
- **ShareGate Growth**: Scaling the ShareGate product line for M365 administration and security.

## Why Work Here
- **Remote-First & Flexibility**: Work from anywhere in Canada; work up to 150 days per year abroad. Office in Montreal is optional except for two annual in-person gatherings. [workleap.com](https://workleap.com/careers)
- **Comprehensive Benefits**: Group insurance, $1,300 health & wellness allowance, telemedicine & EFAP, financial support for new parents, home office allowance, internet reimbursement, and delivered meals. [workleap.com](https://workleap.com/careers)
- **Competitive Compensation**: Competitive salary, annual performance bonuses, 5% RRSP contribution, and referral bonuses. [workleap.com](https://workleap.com/careers)
- **Learning & Growth**: Training, conferences, language courses, and a focus on career development.
- **Engineering Culture**: Emphasis on written, asynchronous communication; proactive communication principles; and a strong focus on sustainable, high-performance collaboration. [workleap.com](https://workleap.com/careers)
- **Values-Driven**: "Walk the talk" on employee experience, with a strong internal focus on caring for own team before serving customers.

## Sources
1. [Workleap About Page](https://workleap.com/about)
2. [Workleap Careers Page](https://workleap.com/careers)
3. [Workleap Job Board (Greenhouse)](https://job-boards.greenhouse.io/workleap)
4. [Workleap Homepage](https://workleap.com/)
5. [Workleap LinkedIn](https://ca.linkedin.com/company/workleaphq)

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