Senior Technical Support Specialist

Match Marketing Group; Mississauga; On-site; CAD 70,000 - 90,000; Full time

Job summary

A leading retail agency seeks a Senior Technical Support Specialist to drive technical excellence by resolving complex issues and training users in new technology. The role requires strong interpersonal skills and in-depth IT knowledge, ensuring effective support across the organization.

Qualifications

• 3-5 years experience in IT, preferably in retail settings.
• Strong communication and task prioritization skills.
• Confidence in proposing ideas to enhance user experiences.

Responsibilities

• Troubleshoot and resolve complex hardware and software issues.
• Lead user training on new technologies and coordinate with IT.
• Develop documentation and recommendations for technology systems.

Skills

Networking fundamentals

Windows troubleshooting

macOS troubleshooting

Microsoft Office

Office 365 management

Google Workplace management

Windows Server management

Interpersonal skills

Education

Industry Certifications (CompTIA, Security+, Microsoft 365)

Tools

InTune

JAMF

Job description

Overview

Job Title: Senior Technical Support Specialist

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 Senior Technical Support Specialist, you’ll play a pivotal role in driving technical excellence across the organization. You will proactively troubleshoot and resolve complex hardware and software issues, lead user training on new technologies, and collaborate with cross-functional teams to maximize the adoption and impact of IT solutions. This role demands both deep technical expertise and strong interpersonal skills to deliver an exceptional support experience and ensure our teams are empowered by the tools they use every day.

Role & Responsibilities:

• Proactively identify, analyze, and present recommendations to resolve complex hardware and software issues.
• Work with the IT & staff across the greater agency to further adopt usage of technology systems that are available, and write documentation/runbooks for both audiences.
• Perform software technical orientation (ability to introduce/train new staff on the use of new software being introduced across the organization)
• Escalate issues to the proper level/areas of support when necessary.
• Coordinate with management on initiatives that result in intuitive experiences and excitement about the use of our space.

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

• Confident– 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.
• Effective– The candidate must prioritize tasks and communicate the status of projects to both the staff and IT group.
• Personable– The candidate develops relationships with both the user and external-partner communities using effective communication to solve their concerns.
• 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)

Skills/Abilities:

• In depth knowledge of networking fundamentals (TCPIP, VLANs, Routing, etc)
• In depth knowledge of Windows and macOS and troubleshooting.
• In depth knowledge of the Microsoft Office suite
• 3+ years managing and configuring Office 365 and Google Workplace platforms; along with their associated applications.
• 3+ Years configuring and managing Windows and macOS MDM solutions (InTune & JAMF specifically)
• 2+ Years managing Windows Server with focused experience in Active Directory, Group Policy, File Access Control Lists and Sharing
• Industry Certifications such as CompTIA, Security+, Microsoft 365, Google, Apple, etc.

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

• 3-5 years of experience in the IT field, preferably in a Retail/field settings.
• 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.

We thank all applicants for their interest; only those selected for interviews will be contacted. Match Retail is proud to be an equal opportunity employer. We celebrate diversity and are committed to fostering an inclusive environment for all.