IT Support Technician

Position: IT Support Technician (6-month Contract)

This role is listed as remote with access to the Montreal office
, which provides meaningful flexibility — but it comes with important caveats for nomads and location-independent workers.

The job requires bilingual French/English fluency and is restricted to Canada only
, which significantly limits where you can legally work. Canadian tax residency and labor law compliance are almost certainly expected. This is not a globally-open remote role — digital nomad visas in places like Portugal or Thailand would not satisfy employment eligibility here.

• Timezone: No explicit timezone requirement is stated, but supporting internal Canadian employees implies core Eastern or Pacific hours. Significant timezone deviation (e.g., Southeast Asia) would create friction with real-time IT support needs.
• Async-friendliness: Moderate. The team communicates primarily via Slack and values autonomy, but IT support is inherently reactive and time-sensitive — full async is unlikely.
• Salary context: CAD $68K–$85K is roughly USD $50K–$63K at current rates. That's comfortable for lower-cost Canadian cities (Halifax, Winnipeg) but tight for Toronto or Vancouver. For nomads based legally in Canada, mid-sized cities offer good value.
• Travel perks: Two in-person team gatherings per year are covered — a lightweight travel commitment that suits nomads with a Canadian base.

Bottom line: this is best suited to someone based in Canada who prefers remote flexibility within the country, not a true location-independent nomad arrangement.

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, and Share Gate , the world's leading solution for Microsoft 365 migration and governance. More than 15,000 companies worldwide trust us. 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

You're at the heart of the employee experience, delivering reliable, human, and efficient support to everyone 'll handle a wide range of requests — from access and SaaS tools to endpoint administration — with one simple goal: help fast and help well. Every day you solve technical issues and document what you learn so the whole team benefits. If you spot a better way to run a process or tool, you propose it and we try it quickly.

You'll work hand in hand with the team on incidents and one-off projects, keeping your priorities clear in an environment that moves fast.

Your Impact

• Deliver reliable, human support to every Workleap employee so they get back to being productive quickly and the employee experience stays a top priority.
• Own access and SaaS tool management so every new hire is ready on day one and our access stays secure.
• Maintain the device fleet (rotation, deployment, inventory) to keep equipment reliable and up to date for the whole team.
• Document and structure the team's knowledge to cut repeat requests and help everyone resolve issues faster.
• Use AI in your daily work (Claude, Slack automations, skills) to speed up request resolution and free up time for higher-value projects.
• Drive process and tool improvements to boost team efficiency and the user experience.

Your Team

Over the next few months, our priority is to deliver fast, human, and consistent support to a company in transformation, while cutting down repetitive work. Concretely, we're rolling out One Login to simplify how employees access their tools, and we're automating request coordination. The challenge is keeping the experience great…