Senior IT Engineer

Third Octet • Mississauga, ON

6d • CA$80,000 - CA$99,000 • Hybrid

About The Position

This role serves as the terminal operational escalation point for the Services team, taking technical command during major incidents, directing diagnosis, deciding actions, and keeping leadership informed. The Senior IT Engineer is responsible for executing complex changes beyond established standards safely, with rollback planned, and remediating environments back to standard and keeping them there. This position also involves running post-incident reviews that lead to tangible improvements in standards, runbooks, or automation, and deliberately developing Tier 2 analysts. Approximately 40-50% of the time will be dedicated to delivering change, including leading migrations, server and cloud transitions, and new customer onboardings, implementing Workplace OS layers to defined standards, and validating that new builds are operable before handover. The role requires diagnostic rigor under pressure, design judgment with deference to standards, risk calibration, a default to teaching, and the ability to translate technical information clearly. The company is a Canadian managed IT services provider working with small to mid-sized businesses, typically 25 to 150 employees, across the Greater Toronto Area and beyond. Their Workplace Suite is built on Microsoft 365, Microsoft Azure, Cisco Meraki, Barracuda, and Lenovo, and they are expanding it into Workplace OS.

Requirements

• Five or more years supporting and engineering Microsoft environments, with real time in a managed services or multi-customer setting
• A track record of owning complex problems end to end, and of executing change in production without incident
• Microsoft 365 in depth: Exchange Online, Teams, SharePoint, Intune, Defender, Purview fundamentals
• Entra ID and Active Directory in depth — hybrid identity, authentication flows, Conditional Access
• Windows Server: AD, Group Policy, DNS, DHCP, file services, certificates
• Azure infrastructure: virtual machines, networking, storage, backup, Site Recovery, governance and cost
• Security in practice: MFA, Conditional Access, endpoint protection, patch and vulnerability management, Zero Trust, CIS familiarity
• Networking to a genuine troubleshooting standard. Cisco Meraki and Barracuda are directly relevant.
• PowerShell for administration and automation
• Backup, continuity, and DR — designing it and proving it works
• Diagnostic rigour under pressure. Staying systematic when a customer is down and everyone is watching.
• Design judgement with standards deference. You know what good looks like and you still choose the standard over your own preference.
• Risk calibration. Blast radius, rollback, and the discipline to stop.
• Teaching by default. You leave the team more capable than you found it.
• Plain-language translation. Explaining technical reality without condescension and without false comfort.
• Interest in automation. You do not have to be a developer. You do have to notice repetition and want it gone.

Nice To Haves

• Valued certifications: Microsoft endpoint and administrator paths, the SC series, AZ-104 / AZ-305 / AZ-500

Responsibilities

• Act as the terminal operational escalation point for the Services team
• Take technical command during major incidents: direct diagnosis, decide actions, keep leadership informed
• Execute complex change beyond established standards, safely, with rollback planned
• Remediate environments back to standard and keep them there
• Run post-incident reviews that actually change something — a standard, a runbook, an an automation
• Develop our Tier 2 analysts deliberately, not incidentally
• Lead migrations, server and cloud transitions, and new customer onboardings
• Implement our Workplace OS layers to defined standard
• Validate that what gets built can be operated by the team, and hand it over properly

Benefits

• 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
• Broad exposure to technology through client engagements and lab environments
• 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
• A defined career framework with development plans, capability bands, and protected development time
• An open voice in shaping the direction of the company, with leadership that serves your best interest

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed