IT Support Specialist - Head Office (Yorkdale)

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

Who We Are

Retailors is a leading and rapidly expanding retailer specializing in the sports and athleisure industry. We are proud to be the global partner of choice for operating Nike retail locations across Canada, Europe, Australia, New Zealand, and Israel.

As part of the Fox Group, Retailors Canada continues to expand its footprint across the country. Our IT team plays a critical role in supporting this growth by delivering reliable technology solutions that keep our Head Office and retail operations running efficiently.

Who We're Looking For

We are seeking an experienced IT Support Specialist to join our Head Office team. This role provides technical support across all five of our brands, working closely with both Head Office employees and retail store teams. The ideal candidate is a proactive problem solver, an exceptional team player, and thrives in a fast-paced retail environment.

Responsibilities Include, But Are Not Limited To

• Provide front-line technical support to onsite and remote end users.
• Support Point-of-Sale (POS) systems, cash register environments, and ERP systems.
• Administer and troubleshoot Microsoft 365 Exchange Online and Microsoft Intune.
• Manage and maintain Active Directory (AD) and Azure Active Directory (AAD)/Microsoft Entra ID.
• Support Microsoft Azure servers, virtual machines, and Windows operating systems.
• Install, configure, and troubleshoot HP Retail hardware, including touchscreens, receipt printers, barcode scanners, and HP/Dell desktops and laptops.
• Support network printers and resolve general network connectivity issues.
• Troubleshoot and support networking technologies, including:
• VLANs
• SSL tunneling
• SSL clients
• Network switching
• Wi‑Fi
• Firewall policies
• Provide technical support to retail stores during weekends, holidays, and outside regular business hours, as required.
• Travel between retail locations to support day‑to‑day operations and new store openings.
• Assist with the setup and deployment of new retail stores in a fast‑paced environment.
• Support Mobile Device Management (MDM) solutions, including ManageEngine MDM, Apple device management, and Android device management (asset).

Qualifications

• Minimum of proven five (5) years of experience providing end‑user and remote technical support (mandatory).
• Proven hands‑on experience supporting ERP systems and retail Point‑of‑Sale (POS) environments (mandatory).
• Strong experience administering Microsoft 365 Exchange Online and Microsoft Intune.
• Experience managing Active Directory (AD) and Azure Active Directory (AAD)/Microsoft Entra ID.
• Strong knowledge of Microsoft Windows operating systems, including installation, troubleshooting, and administration.
• The ideal candidate will have extensive hands‑on experience with Microsoft SQL Server (STD\Express) and a strong

understanding of database architecture, performance tuning, query optimization, and troubleshooting.

(mandatory).

Experience supporting HP Retail hardware, including touchscreens, printers, scanners, and HP/Dell desktops and laptops.

• Experience supporting and troubleshooting network printers.
• Solid understanding of networking concepts, including VLANs, routing, SSL tunneling, SSL clients, switching, Wi‑Fi, and firewall policies.
• Ability and willingness to work flexible hours, including weekends, holidays, and on‑call support when required.
• Valid driver’s license with the ability to travel between retail locations as needed.
• Ability to prioritize multiple tasks and perform effectively in a fast‑paced retail environment.

Work Location

• Primarily onsite at our Head Office located at Yorkdale Shopping Centre.
• Regular travel to retail store locations throughout the Greater Toronto Area is required.
• Additional travel may be required to support new store openings, urgent technical issues, and on‑call support.

Pay range: $50,000 – $58,000

This is a vacant position.

Retailors (Fox Group) is an equal opportunity employer committed to diversity and inclusion, and we encourage applications from all qualified candidates, including those with disabilities. We will accommodate applicants’ needs, upon request, throughout all stages of the recruitment process. Please inform us of the accommodation(s) that you may require. Information received relating to accommodation will be addressed confidentially.

We thank all applicants for your interest in this exciting opportunity; however, only qualified applicants will be contacted