We are looking for an IT Support Specialist to provide dependable technical assistance for retail operations in North York, Ontario. This position supports both on-site and remote employees, helping maintain stable end-user systems, core Microsoft environments, and essential store hardware. The ideal candidate brings strong troubleshooting ability, practical infrastructure knowledge, and experience supporting business-critical technology in a fast-paced setting.

Responsibilities:
• Deliver day-to-day technical support to office-based and remote staff, resolving hardware, software, and access-related issues in a timely manner.
• Administer and support Microsoft 365 services, including user account setup, permissions, and end-user troubleshooting across core applications.
• Maintain and support Microsoft Azure and Windows server environments, while assisting with system performance, user connectivity, and platform reliability.
• Diagnose and resolve issues involving Windows 10 and Windows 11 devices, as well as systems operating in Windows Server 2012, 2016, and 2019 environments.
• Provide support for desktops, laptops, servers, and retail technology such as touch displays, receipt printers, barcode scanners, and other peripheral equipment.
• Manage and troubleshoot network-connected printers and related printing issues across business and retail locations.
• Assist with infrastructure support activities involving VLANs, routing, switching, secure tunnelling, firewall rules, and remote connectivity tools.
• Contribute to virtualization and backup operations, including support for Hyper-V environments and Veeam backup and recovery processes when required.
• Minimum of 5 years of experience providing front-line technical support to both in-person and remote users.
• Hands-on experience administering Microsoft 365 and supporting end users within a Microsoft-based environment.
• Working knowledge of Microsoft Azure, Azure Active Directory, and Windows server platforms.
• Strong troubleshooting skills across desktop systems, computer hardware, and service desk or deskside support functions.
• Experience supporting Windows 10 and Windows 11 operating systems in a business environment.
• Familiarity with retail hardware, including POS-related devices, printers, scanners, and workstation equipment from major manufacturers.
• Understanding of network fundamentals such as VLANs, routing, switching, and printer connectivity.
• Exposure to Hyper-V, Veeam Backup and Restore, and Check Point firewall environments would be considered an asset.

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