[All remote jobs](https://jobicy.com/jobs.md)[![Workleap logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/b84329e1-221.png)](https://jobicy.com/company/workleap.md)[Workleap](https://jobicy.com/company/workleap.md) # IT Support Technician (6-month Contract) AI Summary Workleap is hiring a six-month contract IT Support Technician to provide first- and second-line internal support for a growing, fast-moving organization. The role manages employee access, Microsoft 365 and Entra ID environments, SaaS tooling, endpoint deployment, inventory, and equipment lifecycle across Windows and macOS. The technician will document knowledge, automate repetitive workflows, and contribute to projects such as OneLogin rollout and request coordination automation. Success requires fluent French and English communication, strong service orientation, and comfort working independently in a Slack-centered remote team. The position is remote within Canada, with optional access to the Montreal office and twice-yearly in-person gatherings.[Apply for this job](#job-application)[View company](https://jobicy.com/company/workleap.md)ShareRemote from[Canada](https://jobicy.com/job-region/canada.md)SalaryCAD 68k–85k / yrDepartment[Technical Support](https://jobicy.com/categories/technical-support.md)EmploymentContractExperienceOpen levelPublished6 Nov 2026Apply before6 Dec 2026Listing views36Application actions2Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. Opportunity details ## About this role. ### 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 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 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 Show more [Apply now >](https://jobicy.com/jobs/159415-it-support-technician-6-month-contract.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 3/5EasyHard ### Pace & Pressure 4/5RelaxedFast-paced ### Autonomy Level 4/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThe technical scope covers identity, SaaS access, device administration, and automation, requiring sound troubleshooting across several platforms. The pace is elevated because the team is supporting organizational change while reducing repetitive work. ## Salary analysis Estimated compensation compared with the broader CA market for similar roles. Estimated job median (per year)Highly competitiveC$76,500CA market range (per year)C$60k–C$90k0C$99.00k AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. The employer discloses a CAD 68,000–85,000 base-salary range. The yearly cadence is inferred from the Canadian full-time professional support-role context because the posting does not explicitly state a pay period. Estimated Canadian market pay for a contract IT Support Technician is CAD 60,000–90,000 per year. ## Core skills Skills and capabilities most closely associated with this opportunity. [IT support](https://jobicy.com/jobs?search_keywords=IT%20support.md)[Technical troubleshooting](https://jobicy.com/jobs?search_keywords=Technical%20troubleshooting.md)[Microsoft 365](https://jobicy.com/jobs?search_keywords=Microsoft%20365.md)[Microsoft Entra ID](https://jobicy.com/jobs?search_keywords=Microsoft%20Entra%20ID.md)[Identity and access management](https://jobicy.com/jobs?search_keywords=Identity%20and%20access%20management.md)[SaaS administration](https://jobicy.com/jobs?search_keywords=SaaS%20administration.md)[Single sign-on](https://jobicy.com/jobs?search_keywords=Single%20sign-on.md)[Mobile device management](https://jobicy.com/jobs?search_keywords=Mobile%20device%20management.md)[Endpoint management](https://jobicy.com/jobs?search_keywords=Endpoint%20management.md)[Windows](https://jobicy.com/jobs?search_keywords=Windows.md)[macOS](https://jobicy.com/jobs?search_keywords=macOS.md)[Device lifecycle management](https://jobicy.com/jobs?search_keywords=Device%20lifecycle%20management.md)[Knowledge base documentation](https://jobicy.com/jobs?search_keywords=Knowledge%20base%20documentation.md)[IT automation](https://jobicy.com/jobs?search_keywords=IT%20automation.md)[French and English communication](https://jobicy.com/jobs?search_keywords=French%20and%20English%20communication.md) Sample interview questionsHow would you prioritize several simultaneous IT support requests from employees?I would assess business impact, urgency, security risk, and the number of people affected. I would address access outages and security-related issues first, communicate expected timelines, and document updates in the ticketing system. Describe your approach to onboarding a new employee from an IT perspective. I would follow a standardized checklist covering account creation, least-privilege access, device provisioning, required SaaS applications, MFA, and orientation materials. I would verify that the employee can access essential tools before their first day and record asset assignment accurately. How have you reduced repetitive support work? I identify recurring request patterns through ticket data and user feedback, then create clear self-service documentation or automate the workflow. For example, I would use Slack workflows, identity groups, or scripts to streamline common access and equipment requests. What steps would you take to troubleshoot a Microsoft 365 access problem? I would confirm the user’s symptoms and scope, check account status, licensing, MFA, group membership, conditional-access policies, and service health. I would test the least disruptive resolution, communicate progress, and document the root cause and fix. How do you maintain high-quality support in a bilingual remote environment? I communicate clearly in the requester’s preferred language, acknowledge requests promptly, and avoid unexplained technical jargon. I use consistent documentation, transparent status updates, and structured handoffs so that colleagues receive the same quality of service regardless of channel or language. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. 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