Senior Technical Support Specialist

Windsor, ON
On-site
Posted Sep 30, 2026
1 position

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Employment type: Contract
Experience level: Mid-level · 2+ years
Posting language: English
Working hours: 40 hours per week
Seniority: Associate
Application method: Direct apply is available

Job summary

Provide onsite first- and second-level technical support to employees, troubleshooting computers, laptops, mobile devices, software, peripherals, and network-related issues. Deploy and maintain endpoint devices, manage inventory and user access, support onboarding and office moves, and document recurring issues and resolutions.

Job details

OnX Canada is working with a major health insurance provider seeking a customer-focused and technically skilled L2 Technical Analyst to provide exceptional support to employees across corporate environments. This is an initial 6-month contract - with the ability to extend or transition to fulltime. This role requires your fully onsite at our client's head office in Windsor, Ontario. The successful candidate will assist with device deployments, onboarding and offboarding activities, asset management, inventory tracking, and day-to-day IT operations. The role also supports office moves, workstation deployments, equipment installations, and other hands-on IT activities to ensure employees have the tools and technology required to work effectively. This position offers excellent exposure to enterprise technologies including Microsoft 365, Intune, Entra ID, endpoint management, networking, cybersecurity, and IT infrastructure, making it an ideal opportunity for someone looking to grow their career in systems administration and IT operations. Roles & Responsibilities Work directly with the WT&DEX team to provide technical support to staff located Windsor Provide first and second level Help Desk support onsite to our offices as part of our onsite essential services team. Troubleshoot problems reported by customers in various business areas and Information Technology related to desktop computers, laptops, and mobile devices. Help maintain inventory, build, and deploy endpoint devices following documented and automated procedures ensuring the highest levels of quality are maintained throughout the asset’s life cycle. Assist customers in the setup and configuration of their personal computer or related endpoint devices. Provide instructions to customers regarding the basic use of personal computers and the corporate network. Install software products and product upgrades on personal computers or related devices. Research new personal computer products for prospective use. Read industry publications regarding the provision of personal computer technical support. Assist Network & Host Computing Infrastructure staff as required. Align with corporate policies. The ability and willingness to work extended hours to provide onsite and remote support is required. Must-Have Skills & Qualifications Prior experience providing end-user technical support in a corporate, healthcare, retail, or managed services environment. Strong troubleshooting experience supporting Windows 11 desktops and laptops. Experience supporting Microsoft 365 applications including Outlook, Teams, OneDrive, Copilot, PowerBI, and SQL Server. Knowledge of Active Directory and user account administration, including password resets, account unlocks, group membership management, and MFA support. Experience performing workstation deployments, hardware installations, asset management, and user onboarding activities. Windows Server Remote Desktop Support Experience configuring and troubleshooting printers, peripherals, docking stations, monitors, and mobile devices. Support employee onboarding and offboarding activities, including account provisioning, access management, device deployment, and asset recovery. Coordinate new hire setup by preparing laptops, peripherals, software, user accounts, and required system access. Maintain accurate asset inventory, equipment assignments, software licensing records, and technical documentation while creating knowledge base articles and documenting recurring issues and resolutions. Strong customer service and communication skills with the ability to explain technical concepts to non-technical users. Ability to prioritize competing requests and work independently in a fast-paced environment. Valid G driver's license and ability to travel between office, clinic, and pharmacy locations as required. Physical Requirements Ability to safely lift, carry, and move IT equipment weighing up to 50 pounds. Perform workstation deployments, desk setups, and hardware installations in office environments. Assist with office relocations, desk moves, technology refreshes, and equipment transfers between locations. Ability to work under desks, connect cabling, install monitors, docking stations, and peripheral equipment as required.

What you’ll do

Requirements

Candidates need corporate or comparable end-user support experience, strong Windows 11 and Microsoft 365 troubleshooting skills, and familiarity with Active Directory, remote desktop support, device deployments, and asset management. Strong customer service, the ability to work independently and extended hours, a valid G driver's license, and the ability to lift and move equipment weighing up to 50 pounds are required.