IT Desk-side Technician

Foresters Financial; Toronto; On-site; CAD 47,000 - 69,000; Full time

Job summary

Foresters Financial is seeking an IT Desk-side Technician to provide hands-on and remote IT support for hardware, software, and business apps. The role includes imaging, deploying devices, and assisting with Copilot AI tools to boost productivity.

The position emphasizes incident management, service requests, and collaboration with IT teams on upgrades and training. A tech degree and 2–5 years of experience are preferred.

Qualifications

• Postsecondary diploma or bachelor's degree in a related technical field.
• 2-5 years’ experience with end-user device support in a corporate setting.
• Strong problem solving and communication abilities.
• Customer service orientation and managing expectations.
• Understanding of Insurance/Financial/Fraternal industries.
• Client-facing experience and collaborative teamwork.

Responsibilities

• Provide in-person and remote support for applications, devices, peripherals and software.
• Image, install, diagnose, maintain and upgrade PC equipment.
• Analyze complex hardware and software issues to identify trends and preventative actions.
• Offer end-user support and AI guidance for Microsoft Copilot, including training.
• Create reports and data for ticket management, asset management and cost control.
• Contribute to projects and upgrades with cross-functional teams.
• Develop QA processes for deployments, training guides and end-user sessions; participate in DR drills.
• Potential after-hours support and light travel.

Skills

End-user support

Customer service

Problem solving

Communication

Teamwork

Remote support

AI guidance

Time management

Education

Postsecondary diploma

Bachelor's degree in CS/IT

ITIL Foundation

MS-900

AZ-900

Azure Fundamentals

Tools

Windows OS

Microsoft 365

Exchange

Active Directory

Azure Portal

Intune

Remote support tools

PC Imaging

Job description

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.

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 (MS-900) an asset
• Microsoft Certified: Azure Fundamentals (AZ-900) an asset

Salary Range

$47,300.00 - $69,300.00

The actual base salary for this position will depend on several factors, including job-related skills, experience, and education. In addition to base pay, eligible employees may participate in a discretionary variable incentive plan, results are subject to both individual and company performance.

Please note that this posting is intended to fill an existing vacancy; however, there may be instances where more than one vacancy is available for the same role.

Equal Opportunity Employment and Inclusion –

at Foresters Financial, we are committed to sustaining an equal opportunity environment for all job applicants. We embrace Inclusion, Diversity and Equity (IDE) as a core strategic objective for building strong, innovative teams in which all our employees can show up wholly and authentically as themselves.

Foresters Financial strives to provide an accessible candidate experience for prospective employees with different abilities. If you anticipate needing any type of accommodations during the recruitment process, please email [e-mail] in advance of your appointment.

Thank you for choosing Foresters. Only those candidates who will be selected for further consideration will be contacted by our Talent Acquisition Team.