Technical Support Specialist

Location: Mississauga, ON (Hybrid)
Schedule: Monday to Friday

Salary: $60,000 to $70,000

We are actively hiring for this position  

About Match Retail

Match Retail is a leading sales, training, and branded retail agency trusted by North America's most recognizable brands. We help companies thrive in retail through powerful customer engagement and scalable talent solutions. Our people are our edge—trained, supported, and empowered to make an impact where it matters most: in-store.

About the Role

As a Technical Support Specialist, you’ll be the go-to resource for frontline tech support—ensuring our teams across North America have a seamless technology experience. From onboarding new hires with the right tools to troubleshooting complex hardware and software issues, you'll play a vital role in keeping the organization running smoothly. You'll bring a solutions-first mindset, deliver exceptional support, and own the end-user tech experience in your local office. This role is ideal for someone who thrives on problem-solving, loves working with people, and can juggle multiple priorities with confidence and precision.

Role & Responsibilities:

• Provide clear and concise day-to-day hardware and software technical support for our employees across North America. Including Mac and Windows laptop troubleshooting, SaaS configurations and administration, and implementing permanent solutions to recurring technical issues.
• Hardware and software installation and configuring, including the creation of computer and SaaS accounts for employee new hires and departures.
• Utilize and update internal trouble ticketing system with a clear breakdown of steps taken resolve the user issue, providing clear, supportive, and ongoing communication with the user throughout the ticket lifecycle.
• New employee technical orientation, demonstrating to the user our hardware, SaaS offerings, and technical support portals.
• Escalate issues to the proper level/areas of support when necessary.

In addition to the job responsibilities, the ideal candidate must possess the following qualities:

• A desire to improve – The candidate learns and expands technical knowledge and produces ideas with confidence to enrich our users’ technical experiences.
• Dependable – The candidate is accountable to find answers for difficult challenges and delivering solutions.
• Approachable – The candidate is someone that all staff members know they can communicate with to receive consistent, friendly, and clear support throughout their request for support.
• Effective – The candidate must prioritize tasks and communicate the status of projects to both the staff and IT group.
• Detailed – The candidate focuses on the required details of their tasks to ensure accurate completion of all requirements for the position (including updating documentation/inventories and accurate timesheets)

Skills/Abilities:

• Knowledge/Ability to troubleshoot hardware issues and computer/systems diagnostics.
• Knowledge of basic networking fundamentals (TCPIP, Subnetting, DHCP, etc.)
• Knowledge of Windows and macOS troubleshooting (OS, Settings and File Permissions)
• Knowledge of usage and troubleshooting the Microsoft Office suite
• Knowledge/Exposure to the Office 365 platform and associated applications (OneDrive, Teams, SharePoint, InTune, Azure Active Directory, etc.)
• Knowledge of Windows Server platform fundamentals (Active Directory, Group Policy, File Access Control Lists, etc.)
• Knowledge of Jamf MDM fundamentals for macOS/iOS/iPadOS
• Knowledge to troubleshoot issues within the Adobe Creative Cloud suite
• Industry Certifications such as CompTIA, Security+, Microsoft 365, etc.

In addition to Technical Skills, the ideal candidate must possess the following qualities:

• 2-3 years of experience in the IT field, preferably with supporting end user hardware, SaaS administration, and executing new user creation and hardware configuration.
• 2-3 years of experience with Windows Server administration.
• 2-3 years of experience with ITSM tools such as Jira Service Management or Freshdesk.
• 2-3 years of experience with Office 365 administration.
• 2-3 years of experience in Google Workspace administration.   
• 2-3 years of experience with Windows/OSX MDM toolsets such as Jamf, Kengi, Intune and Autopilot.
• 2-3 years of experience with remote management tools such as TeamViewer and Splashtop.
• Confidence in expanding technical knowledge and proposing ideas to enhance user experiences.
• Dependability in seeking solutions to challenging issues and delivering results.
• Effectiveness in task prioritization and communication of project statuses to both staff and IT teams.
• Strong interpersonal skills to build relationships with users and external partners, effectively addressing their concerns.

Why Join Match Retail?

• Opportunity to work with leading national and global brands
• Collaborative, performance-driven culture
• Competitive compensation and benefits
• Career growth and professional development opportunities

Interview Process

Our recruitment process is structured and transparent, with candidates assessed consistently against role-related criteria.

Step 1: Qualified candidates complete an initial virtual interview with a Talent Acquisition Specialist.
Step 2: Shortlisted candidates participate in a virtual or in-person interview with the Hiring Manager.
Step 3: Selected candidates attend an in-person or virtual interview with the Head of IT. 
Step 4: Final candidates participate in an in-person or virtual interview with the Senior Leadership. 

AI Disclosure

We use AI-assisted tools to help screen resumes for key skills and minimum requirements relevant to the role. All results are reviewed by our hiring team to ensure thoughtful and balanced decision making. 

Match Retail is an equal opportunity employer. We celebrate diversity and are committed to fostering an inclusive environment for all.