IT Systems Technician

Rockport Commercial Inc.•Winnipeg, MB

29d•Onsite

About The Position

Rockport Investment Group is a family-owned real estate development and investment firm based in Winnipeg that has been building communities since 1975. As the parent company to specialized divisions like Rockport Commercial Inc., we manage the entire property lifecycle—from land acquisition and construction to long-term leasing and property management for commercial, industrial, and multi-family residential projects. We pride ourselves on our collaborative, family-oriented culture that focuses on quality development and internal professional growth. We’re looking for a sharp, adaptable IT professional to join our team as the go-to resource for day-to-day technical support across Rockport Investment Group and Rockport Commercial. This isn’t a rigid helpdesk position—no two days look the same, and we need someone who’s comfortable jumping between a printer jam, a network cable run, and an Outlook configuration without missing a beat. You’ll work closely with our IT Manager, handling the full spectrum of L1 and L2 support for internal staff. Anything that can’t be resolved at your level gets escalated directly to the IT Manager—but the expectation is that you’re solving most of what comes your way independently.

Requirements

Solid hands-on IT support experience, particularly with Windows environments and Microsoft 365 (Outlook/Exchange).
Comfortable troubleshooting a wide range of issues independently—printers, phones, cameras, networking, and everything in between.
Experience with physical networking tasks (cable termination, hardware installs).
A self-starter who communicates well, takes initiative, and genuinely enjoys helping people.

Nice To Haves

Scripting & Automation: PowerShell and/or Python experience is a strong bonus—if you’ve automated something to make your life easier, we want to hear about it.
Excel: Strong Excel skills are a big plus. We work with a lot of data and appreciate someone who knows their way around a spreadsheet.
Web Development: Familiarity with JavaScript/TypeScript and basic web development is considered a strong asset.
Virtualization: Experience with Docker, XCP-NG, Hyper-V, or ESXi.
M365 Administration: Hands-on experience managing an M365 tenant including Exchange, Intune, Purview, and Azure.
MSP Background: Previous experience at a Managed Service Provider—you likely already know how to handle volume and variety.

Responsibilities

Staff Support: First point of contact for all internal IT requests—troubleshooting Windows, Outlook/Exchange, mobile devices, and general day-to-day tech issues.
Development & Programming: Proficiency in Python, PowerShell, and/or any other scripting language to assist with basic software development, custom coding to streamline workflows, and the manipulation of Excel/spreadsheet data.
Hardware & Systems: Keep office equipment running smoothly, including phone systems, printers, and peripheral hardware.
Onboarding & Offboarding: Handle the full technical lifecycle for staff—setting up workstations, provisioning accounts and software access, deploying devices for new hires, and cleanly deprovisioning everything when someone moves on.
Security & Surveillance: Maintain on-site camera systems and surveillance equipment across our managed properties.
Physical Networking: Hands-on cabling work including RJ45/Coax termination and hardware installations.
Systems Support: Assist the IT Manager with Windows environment configurations, internal tooling, and digital asset management.
Training & Communication: Help colleagues get comfortable with technology—whether it’s walking someone through a software update or explaining a new process. Strong communication matters here.