IT Desk-side Technician
foresters · Toronto, Ontario · Canada · On-site
Pay: CAD 47,300 – 69,300 a year
Posted Aug 26, 2026
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Career Opportunity
Role Title
IT Desk-side Technician
Purpose of role
A Foresters IT Desk-side Technician provides hands-on and remote IT support to ensure employees can work effectively with their hardware, software, and business applications. The role is responsible for troubleshooting complex technical issues, supporting device deployments, onboarding and refresh activities. Managing incidents, service requests, and helping improve IT processes to minimize business disruptions. The position also collaborates with other IT teams on projects, upgrades, recovery activities, and technology initiatives such as Microsoft Copilot and end-user training.
Job Description
Key Responsibilities
Providing in-person and remote support for technical application resolution, end user computing, peripherals and software.
Imaging, installing, diagnosing, maintaining, and upgrading all PC equipment.
Analyzing complex hardware and application issues to identify trends and implement preventative solutions documenting them as required for review, revision, and approval.
Provide end-user support and AI guidance for Microsoft Copilot, including troubleshooting issues, delivering training, and helping employees leverage AI tools to improve productivity and streamline daily business tasks.
Creating reports and presenting data metrics for ticket management, workflow, asset management and cost control.
Contribute to project implementation and upgrade initiatives, collaborating with cross-functional teams to reconcile needs and maximize efficiency.
Developing Quality Assurance Process for application testing, end-user computer deployments, training guides and how-to sessions. Participating in disaster recovery planning and restoration exercises, ensuring business continuity in the event of IT failures
Potential after hours support and light travel
Key Qualifications
Postsecondary diploma or bachelor's degree in Computer Science, Information Technology, Computer Systems Technology, or a related technical field
2-5 years’ experience with end-user device support within a corporate environment
Superior problem solving and communication skills
Customer service orientation and capability to manage customer expectations
General understanding of the Insurance, Financial and Fraternal industries
Demonstrable experience working in a client-facing position
Ability to work individually and as a team, managing time effectively
Strong experience in the Microsoft product suite including Windows and Microsoft365
Remote support/tools knowledge
General understanding and experience with AI software, particularly Microsoft Copilot
Exchange/Active Directory/File Share management/Azure Portal/Intune
Thorough (Expert) knowledge and support experience with Microsoft infrastructure and Windows Operating Systems, remote access, email, printers, PC Imaging, and network technologies
ITIL V3 Foundation Level Certified an asset
Microsoft 365 Certified Fundamentals…