When our Senior Support Analysts cannot resolve something, it comes to you - and when you cannot resolve it, the question is no longer "who troubleshoots better," it is "what should the standard be." You are also the person who keeps our customer environments operable and conformant to standard: correcting drift, executing the complex changes, and - importantly - holding the authority to stop something that would leave the team supporting a mess. If you can see that a deliverable will generate six months of support pain, we want you to say so and stop it.

Take technical command during major incidents: direct diagnosis, decide actions, keep leadership informed Run post-incident reviews that actually change something - a standard, a runbook, an automation roughly 40-50% of your time, with a dedicated Implementation Engineer seat planned as this work grows) Lead migrations, server and cloud transitions, and recent customer onboardings Five or more years supporting and engineering Microsoft environments, with real time in a managed services or multi-customer setting Technical depth Microsoft 365 in depth: Exchange Online, Teams, SharePoint, Intune, Defender, Purview fundamentals Windows Server: AD, Group Policy, DNS, DHCP, file services, certificates Azure infrastructure: virtual machines, networking, storage, backup, Site Recovery, governance and cost Networking to a genuine troubleshooting standard. Microsoft endpoint and administrator paths, the SC series, AZ-104 / AZ-305 / AZ-500 Staying systematic when a customer is down and everyone is watching. Risk calibration.

Plain-language translation. Explaining technical reality without condescension and without false comfort. The work is needed and you will see your impact immediately.



And you are joining a team that has just redesigned how it operates specifically so that this role is not the impossible everything-seat it can become elsewhere - escalation and project delivery are explicitly bounded, and a dedicated implementation seat is planned as that work grows.

Implementation

Engineer, if delivery is your preference; You will have a development plan, technical direction from our Architect, and protected time to grow. Personally tailored benefits - health, vision, dental, and paramedical Flexibility in how, when, and where you work across a 4.5-day workweek, with a vacation policy well above standard Focus windows that protect deep, uninterrupted work Funded lifelong learning: an immersive education platform, vendor training, and soft-skills development Wellness support, including access to the employee wellness platform and a wellness allowance An open voice in shaping the direction of the company, with leadership that serves your best interest We are a Canadian managed IT services provider, working since 2007 with small and mid-sized businesses - typically 25 to 150 employees - across the Greater Toronto Area and beyond.

Our Workplace

Suite is built on Microsoft 365, Microsoft Azure, Cisco Meraki, Barracuda, and Lenovo, and we are expanding it into Workplace OS: a deliberate operating model that layers shared visibility, governed automation, insights, and AI onto a secure, standardized foundation. We are a small team supporting a growing base of customers, which means the work is real, the ownership is genuine, and what you build actually gets used. We use automated tools to help sort and shortlist applications.

This posting is for an existing vacancy. #

📌 Senior engineer technical support engineering (Mississauga)
🏢 Third Octet
📍 Mississauga