IT Support Technician (6-month Contract)

Workleap; United States; Hybrid; USD 48,000 - 60,000; Full time

Benefits offered by this job

Family health insurance

Telemedicine

Annual wellness budget

Flexible vacation policy

Remote work with Montreal office

In-person gatherings twice a year

Claude access

Job summary

Workleap Inc. is seeking an IT Support Specialist to deliver human, efficient support across the company in both French and English. You’ll manage access controls, SaaS tools, and the device fleet while collaborating with a team that moves fast.

You’ll document workflows, automate repetitive tasks, and leverage AI to resolve requests quickly. The role emphasizes improving processes, supporting seamless onboarding for new hires, and maintaining secure, scalable access across Microsoft 365 and

Qualifications

• Fluent in French and English, spoken and written.
• Solid first- and second-line IT support experience.
• Comfort with Microsoft 365 / Entra ID environments, access management, and SaaS tools.
• Knowledge of device fleet management (Windows and macOS).
• Builder mindset: document, structure, and automate repetitive work.
• Comfort using AI daily to solve problems and build tools.
• Bonus: experience with Jamf, Jira Assets, Slack, or scripting (PowerShell, Python).

Responsibilities

• Deliver reliable, human support to employees to keep productivity high.
• Own access and SaaS tool management for new hires and security.
• Maintain device fleet deployment and inventory across the team.
• Document and structure knowledge to reduce repeat requests.
• Use AI tools to speed up resolution and enable higher-value projects.
• Propose and implement process and tool improvements.

Skills

French & English

IT support

Microsoft 365 / Entra ID

Device fleet management

Automation mindset

AI tooling

Jamf

Jira

Slack

Scripting

Job description

Company Descriptionthe company 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 company Agent, our newest solution built to make every manager more effective, 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.

Your roleYou're at the heart of the employee experience, delivering reliable, human, and efficient support to everyone at the company. 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 the company 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.

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

At the company, 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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