IT Service Desk Technician - Level 2

Why we are hiring Our client base has grown, and our senior technicians are increasingly needed on projects, onsite work and escalations. We are adding to the service desk so that continues without our response times slipping. This is a growth hire, not a backfill. We are staffing ahead of demand rather than behind it. About us Constant C Technology Group is a Winnipeg based Managed Service and Security Provider. Our clients span manufacturing, logistics, healthcare, insurance, non profit and the arts, so no two days look the same. Our service team is small enough that you will not be a number here. Your work is visible, and so is your impact. Our technicians stay an average of more than six years. In an industry known for turnover, that is the number we are proudest of. We measure what we do. Every technician sees their own numbers each quarter, we talk about them openly, and we use them to decide where to invest in training. If you like knowing where you stand, you will like it here. What you will do Own and resolve tickets across a wide range of client environments, from everyday requests through to the ones nobody else has cracked. Provide advanced remote and onsite support for Windows Server, Active Directory, virtualization (Hyper-V and ESXi) and networking (HP switches, Ruckus APs). Administer client tenants in Microsoft 365 and Azure (Entra ID), including user accounts, mail flow, security policy and SharePoint permissions. Troubleshoot workstation, application and connectivity issues down to root cause, and write it up so the next person does not start from scratch. Work in our RMM (N-able N-central) and PSA (ConnectWise) to manage tickets, deploy solutions and monitor client systems proactively. Support backup platforms (Veeam, Cove) and our 3CX VoIP environment. Build and maintain documentation in our knowledge base. Help newer technicians come up to speed. Some of the best work here is making someone else faster. Your first 90 days We do not throw people at the phones on day one. Weeks 1 to 3. Training and shadowing. You will work non customer facing tickets while you learn our stack, our documentation and how we run things. No phones yet. Weeks 4 to 8. You join the phone and ticket queues, and our dispatcher begins assigning you regular work. You are carrying real load, with the team around you. Weeks 9 to 12. You are working independently as a full member of the team. Writing documentation others rely on, going onsite to clients, bringing proactive fixes forward instead of waiting for the ticket, and helping on project deployments. What we are looking for We are not expecting every box below to be ticked. If you have the essentials and a track record of picking things up, we would rather hire you and train the rest. We fund the training and we give you the time. Essential 2+ years in IT support, ideally in an MSP. Strong Windows Server and Active Directory, including user management and Group Policy. Solid Microsoft 365 administration. Working networking knowledge: VLANs, DNS, DHCP and firewalls. Clear written communication. Our clients read our ticket notes, and how you write to them matters as much as how you fix the problem. A humble, hungry, smart mindset. Confident in what you know, honest about what you do not, and easy to work alongside. Able to work full time from our Winnipeg office. Great to have, and teachable if you do not Virtualization with Hyper-V or VMware ESXi. RMM and PSA experience. N-able and ConnectWise are a significant head start. HP switching and Ruckus wireless. Backup platforms such as Veeam or Cove. VoIP, particularly 3CX. Azure and Entra ID beyond day to day user administration. CompTIA Network+ or Security+, or Microsoft certifications. A valid Class 5 Manitoba licence and a reliable vehicle, for onsite visits. What we offer $53,000 to $65,000 base, reviewed annually, with the quarterly bonus on top of that. A quarterly performance bonus once you reach one year with us, based on clear, published targets. You will know exactly how it is calculated. Loyalty bonuses at three years, five years, and every five years after that. We would rather reward people for staying than spend the money replacing them. Health and dental benefits, plus flex days. Company funded training and certifications. We pay for the exam and we give you time to study. Monthly team events. Not a mandatory fun committee, just time together away from the queue. A modern stack: Microsoft 365, Azure, N-able, ConnectWise, Veeam, Cove, 3CX, Auvik. A team where your ideas get heard and acted on. How to apply Send your resume to [email protected]. Tell us in a few sentences about a problem you solved that you were proud of. We review every application, and we will be in touch if your experience looks like a fit.

Resolve a wide range of technical tickets and provide advanced remote and onsite support for servers, virtualization, and networking. Administer Microsoft 365 and Azure tenants while maintaining detailed documentation in the company knowledge base.

Requires at least 2 years of IT support experience, preferably in an MSP environment, with strong skills in Windows Server and Microsoft 365. Candidates must have working networking knowledge and be able to work full-time from the Winnipeg office.

• Health benefits • Dental benefits • Flex days • Company funded training and certifications • Quarterly performance bonus • Loyalty bonuses • Monthly team events

• Microsoft AzurePreferred

Identified from the job description. Confirm important requirements above.

• Windows Server
• Active Directory
• Microsoft 365 Administration
• Azure
• Entra ID
• Networking
• Hyper-V
• VMware ESXi
• N-able N-central
• ConnectWise
• Veeam
• Cove
• 3CX VoIP
• VLANs
• DNS
• DHCP

• Technology
• Customer Service & Support
• Consulting
• Security & Safety

Minimum education

Professional degree

Minimum experience

2+ years

Apply by

Feb 15, 2027

Posting language

English

Working hours

40 hours per week

Seniority

Entry level

Application method

Direct apply is available