Retail IT Support Specialist - POS & Cloud Systems

RETAILORS; Toronto; On-site; CAD 50,000 - 58,000; Full time

Job summary

Retailors is seeking an experienced IT Support Specialist to join our Head Office team in Toronto. This role provides front-line and remote end-user support across five brands, with a focus on POS, ERP, and Microsoft 365 administration.

You will travel between retail locations in the Greater Toronto Area and support store openings, weekends and on-call hours as required, while maintaining hardware and network infrastructure.

Qualifications

• Five years of end-user and remote technical support experience (mandatory).
• Experience supporting ERP systems and retail POS environments (mandatory).
• Strong experience administering Microsoft 365 Exchange Online and Microsoft Intune.
• Experience managing Active Directory and Azure Active Directory (Entra ID).
• Strong knowledge of Windows operating systems, including installation, troubleshooting, and administration.
• Extensive hands-on experience with Microsoft SQL Server (STD/Express) and database architecture.

Responsibilities

• Provide front-line technical support to onsite and remote end users.
• Support POS systems, cash registers, and ERP systems.
• Administer and troubleshoot Microsoft 365 Exchange Online and Microsoft Intune.
• Manage AD and Azure AD (Entra ID).
• Support Microsoft Azure servers, virtual machines, and Windows OS.
• Install, configure, and troubleshoot HP Retail hardware (touchscreens, printers, scanners, desktops/laptops).
• Support network printers and general network connectivity issues.
• Troubleshoot networking technologies (VLANs, SSL tunneling, SSL clients, switching, Wi‑Fi, firewall policies).
• Provide technical support to retail stores during weekends, holidays, and on-call hours.
• Travel between retail locations to support day‑to‑day operations and new store openings.
• Assist with setup and deployment of new retail stores.
• Support MDM solutions, including ManageEngine MDM and device management for Apple and Android.

Skills

End-user support

Remote support

ERP support

Microsoft 365

Intune

Active Directory

Azure AD

Windows OS

SQL Server

Networking

On-call availability

Driver's license

Tools

ManageEngine MDM

HP Retail hardware setup

Dell/HP desktops and laptops setup

Job description

Retailors is seeking an experienced IT Support Specialist to join our Head Office team in Toronto. This role provides front-line and remote end-user support across five brands, with a focus on POS, ERP, and Microsoft 365 administration.

You will travel between retail locations in the Greater Toronto Area and support store openings, weekends and on-call hours as required, while maintaining hardware and network infrastructure.