About Us
365 Technologies is a Managed Services Provider headquartered in Winnipeg, Manitoba, with a growing presence across Manitoba and Saskatchewan. We support roughly 80 client organizations across a wide range of industries (construction, healthcare, legal, nonprofit, and more) with a team of approximately 25 people who genuinely care about doing this work well.
We operate under the brand Worry-Free IT®, and that's not just marketing copy. It's the standard we hold ourselves to every day. When a client calls us, they're trusting us completely with the technology that runs their business. That responsibility is something we take seriously as a team.
We're investing in how managed IT gets delivered. Our team is actively building AI-assisted documentation, automated onboarding and offboarding workflows, and modern tooling to make our technicians faster and our clients better supported. If you're the kind of person who gets excited about what comes next in this industry, you'll fit in here.
The Role
We're looking for an Network Administrator based in Winnipeg to help us serve our growing client base.
This is a client-facing, technically broad role. You won't be doing the same thing every day. You'll be supporting desktops and servers in the morning, troubleshooting a firewall at a client site after lunch, and documenting a new client environment by end of day. If variety is something you look for, this role delivers.
Reports To: Director of Service Delivery
What You'll Be Doing
- Providing remote support via phone, email, and chat to clients and end-users across the southern Manitoba region, covering workstations, servers, network devices, Microsoft 365, and more
- Conducting on-site visits to client locations across the Winnipeg area as needed for installs, troubleshooting, and relationship maintenance
- Participating in an on-call rotation with after-hours availability per our on-call policy
- Logging detailed, accurate notes in our PSA (HaloPSA) for every ticket. Documentation quality matters here.
- Keeping client environment documentation current in ITGlue
- Responding to and resolving tickets within our published SLAs and communicating proactively when that's at risk
- Escalating effectively to Senior Network Administrators when appropriate
- Tracking time accurately and meeting published KPIs
What We're Looking For
Must-Have
- 3-5 years of active IT support experience, with preference for MSP or multi-client environments
- Strong written and verbal communication skills. You'll be representing 365 directly to clients.
- Solid troubleshooting instincts on Windows 11 and Windows Server (2019, 2022, 2025)
- Experience with implementation and troubleshooting of VoIP telephony solutions
- Hands-on experience with Microsoft 365 administration
- Experience with networking fundamentals: VLANs, routing, DNS, DHCP, firewall configuration
- Ability to manage competing priorities without dropping the ball
Strong Assets
- Experience with endpoint security platforms (we use Huntress)
- Familiarity with PSA/RMM tools (HaloPSA, ConnectWise Manage/Automate, or similar)
- Experience with Veeam Backup and Replication
- Firewall experience with SonicWall or FortiGate
- Hyper-V or VMware virtualization experience
- Experience with deployment/automation tools (we use ImmyBot)
- Microsoft 365 advanced administration including Entra ID, Intune, and SharePoint
What We Offer
- Competitive salary commensurate with experience
- Performance-based incentives
- Comprehensive group benefits package
- Employer RRSP/DPSP/TFSA matching plan
- Health spending account
- Mileage compensation for client site visits
- A team that invests in its own tools and processes. You won't be stuck fighting outdated systems.
One More Thing
We're a 25-person team. That means your work actually matters and is visible. It also means we're not going to hand you a script and a ticket queue and leave you to it. There's real opportunity to grow here, technically and in how you contribute to the business, if that's something you're looking for.
If you're based in Winnipeg and want to be part of building something in this market rather than just filling a seat in it, we'd like to hear from you.
Salary Range: $55,000 to $65,000
