IT Service Technician

365 TechnologiesWinnipeg, MB
CA$45,000 - CA$55,000Onsite

About The Position

365 Technologies is a Winnipeg-based Managed Services Provider with a team of 25, serving 80+ clients across Manitoba and Saskatchewan since 2010. Our tagline is Worry-Free IT® and we mean it -- for our clients and our team. We actively invest in modern and emerging technologies, including AI-powered tools, to deliver smarter, faster support for our clients and our own team. We are looking for a motivated self-starter with a genuine interest in IT and a passion for helping people. This Service Technician will join our service desk team to support our growing client base, working across a diverse range of environments and technologies every day.

Requirements

  • Valid driver's license with daily access to a vehicle
  • Outstanding verbal and written communication skills in English
  • Active listening skills and genuine empathy for clients
  • Ability to juggle multiple tasks in a busy, distraction-prone environment
  • 1-3 years of IT support experience, preferably in a Managed Services environment
  • Experience troubleshooting Microsoft Windows 11
  • Experience with PC and server hardware installation and troubleshooting
  • Working knowledge of IP networking and troubleshooting
  • Comfort learning and working with AI tools in a professional IT context

Nice To Haves

  • Microsoft 365 administration experience, including Copilot and modern workplace deployments
  • Familiarity with SonicWall or Fortinet security appliances
  • Microsoft, CompTIA A+, or Network+ certifications
  • Experience with Microsoft Server OS (2019, 2022, 2025)
  • Experience with Veeam Backup & Replication

Responsibilities

  • Provide on-site and remote support to clients via phone, email, and chat for workstations, servers, network devices, and more
  • Travel to client sites across Winnipeg as needed (mileage fully compensated)
  • Participate in our on-call rotation for after-hours coverage
  • Document all completed work accurately in our ticketing system (HaloPSA)
  • Respond to and resolve tickets within our published Service Level Agreements
  • Communicate proactively with the Service Desk Coordinator or Manager on open incidents and outstanding issues
  • Keep client documentation up to date in IT Glue
  • Track and submit timesheets and expenses accurately
  • Escalate appropriately to Network Administrators, Senior Engineers, or management
  • Hit your targets -- we set clear KPIs and give you the support to reach them

Benefits

  • Competitive compensation with performance-based incentives
  • Comprehensive group benefits package
  • Employer RRSP / DPSP / TFSA matching
  • Health spending account
  • Full mileage compensation for client travel
  • Paid professional development and certification support
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