Careers / Open Role
Systems Administrator
Location: Greater Toronto Area · Hybrid
Type: Full-time
Reports to: [TBD]
Type: Full-time
Reports to: [TBD]
About Wingman
Wingman is a managed IT services provider headquartered in the Greater Toronto Area, supporting growing businesses across Ontario. We work with companies that have outgrown break-fix IT but aren't looking to hand their technology to a faceless national provider. The work we do reflects that — structured, accountable, and built around the way each client actually operates.
About the role
The Systems Administrator is one of the operational engines of the Wingman team. You'll be hands-on with client environments every day — handling support requests, performing maintenance, deploying configurations, and making sure the systems our clients rely on stay healthy and current.
This role is where the technical foundation of managed IT actually happens. You'll work across a portfolio of client environments, develop deep familiarity with the way each one runs, and become the person clients trust to keep things working.
What you'll be doing
- Resolving support tickets across a portfolio of client environments — from password resets and access issues to more complex troubleshooting
- Performing routine maintenance, patching, and updates on client systems
- Deploying and configuring workstations, servers, and network equipment
- Onboarding and offboarding users across client environments — securely and completely
- Managing Microsoft 365, Google Workspace, and core productivity environments
- Maintaining client documentation as the environment changes
- Escalating complex issues to senior team members and learning from how they're handled
- Contributing to the technical standards that define how Wingman operates
What we're looking for
- 2+ years of hands-on systems administration experience in a managed services or IT support environment
- Working knowledge of Microsoft 365, Windows Server, networking fundamentals, and common business productivity platforms
- Comfort supporting both Mac and PC environments
- Strong troubleshooting instincts and willingness to dig into a problem until it's resolved
- Clear communication skills — including the ability to explain technical work to non-technical clients
- Comfort with documentation, follow-up, and the operational hygiene that makes good IT work possible
- Genuine respect for clients, colleagues, and the craft
What we offer
- Competitive compensation, reflective of experience
- Comprehensive benefits package
- Hybrid work model, with regular in-person collaboration in the GTA
- A team that takes the work seriously and invests in the people doing it
How to apply
Send your resume and a short note about why this role interests you to careers@wingmansolutions.com.
We review every application personally. If your background is a fit, we'll be in touch within two weeks.