Workleap

Technical Support IT (6-month Contract)

Canada full-time Mid CAD68,000 - CAD85,000
full-time Mid level Technology & IT Salary listed Curated
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About the role

About ShareGate

ShareGate is the leading Microsoft 365 migration and governance platform, trusted by over 100,000 IT pros for its unmatched simplicity.

It offers the simplest, most reliable, and most affordable way to move business data to Microsoft 365.

Whether migrating from Google Workspace, file shares, Exchange Online, SharePoint On-Premises, or tenant-to-tenant, ShareGate gets the job done, without surprises. From cloud transformation to M&A integration, it keeps things just damn simple.

ShareGate also helps organizations stay in control once their data is migrated. Its powerful governance features let users assess environments, uncover issues, and apply fixes on the spot, so everything stays clean, secure, and optimized. It lays the groundwork for safe Microsoft Copilot deployment within organizations.

ShareGate is developed by Workleap Technologies, a Montréal‑based software company.

Your role
You're at the heart of the employee experience, delivering reliable, human, and efficient support to everyone at Workleap. You'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, and 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 for our colleagues while volumes and needs grow. Our ambition: better documentation, automating what can be automated (Slack, Jira Assets), and making every technician a reliable, autonomous point of contact.
We're a team of seven, made up of technicians, a system administrator, an endpoint administrator, and a manager, working in French and English as needed. We mostly communicate on Slack, directly and without too much ceremony. We share information, help each other out, and stay curious: anyone can suggest improvements or test new tools. We make decisions quickly and adjust along the way.
What you'll bring

Fluency in French and English, spoken and written, since you'll support internal clients who speak both languages;

Solid first- and second-line IT support experience, with a strong sense of service and communication;

Comfort with Microsoft 365 / Entra ID environments, access management, and SaaS tools (SSO, MDM, ticketing);

Knowledge of device fleet management (deployment, inventory, equipment lifecycle) on Windows and macOS;

A builder mindset: you document, structure, and automate repetitive work instead of redoing it by hand;

Comfort using AI daily (Claude, assistants, automations) to solve problems faster and build new tools for the team;

Bonus: experience with Jamf, Jira / Jira Assets, or Slack, or scripting (PowerShell, Python) or no-code automation.

Most of this sounds like you? Apply.
What the job comes with

Base salary: $68 000 - $85 000.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.

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

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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Originally posted on Himalayas

Interview prep

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Mid
Technology & IT Administration API integration Python Remote Collaboration Writing Mid level

Likely questions

  1. Tell us about work you have done that is close to the Technical Support IT (6-month Contract) role.
  2. How would you approach your first 30 days at Workleap?
  3. Which of Administration, API integration and Python have you used recently, and what did it help you achieve?
  4. Describe a time you solved a problem without waiting to be told exactly what to do.
  5. How do you handle busy days, changing priorities, or pressure at work?

Prepare before the call

  • A recent example that proves your experience with Administration, API integration and Python.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Technical Support IT (6-month Contract) role because I can bring practical experience in Administration, API integration and Python, learn the team quickly, and contribute to the outcomes Workleap needs from this hire.

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