Asks for

The ad says“Windows Server and Active Directory: DNS, DHCP, Group Policy, file services”
The ad says“Azure exposure: virtual machines, networking, backup”
The ad says“Azure exposure: virtual machines, networking, backup”
The ad says“Networking good enough to diagnose across the boundary — routing, VLANs, VPN, firewall behaviour. Cisco Meraki and Barracuda experience maps straight onto our stack.”
The ad says“Networking good enough to diagnose across the boundary — routing, VLANs, VPN, firewall behaviour. Cisco Meraki and Barracuda experience maps straight onto our stack.”
The ad says“Practical security: MFA, Conditional Access, and the Microsoft Defender stack”
The ad says“Windows Server and Active Directory: DNS, DHCP, Group Policy, file services”
The ad says“Windows Server and Active Directory: DNS, DHCP, Group Policy, file services”
The ad says“Solid Microsoft 365 administration, including Entra ID — groups, licensing, authentication”
The ad says“Windows Server and Active Directory: DNS, DHCP, Group Policy, file services”
The ad says“Networking good enough to diagnose across the boundary — routing, VLANs, VPN, firewall behaviour. Cisco Meraki and Barracuda experience maps straight onto our stack.”
The ad says“Windows Server and Active Directory: DNS, DHCP, Group Policy, file services”
The ad says“Endpoint management with Intune: policy, compliance, application deployment”
The ad says“Practical security: MFA, Conditional Access, and the Microsoft Defender stack”
The ad says“Solid Microsoft 365 administration, including Entra ID — groups, licensing, authentication”
The ad says“Practical security: MFA, Conditional Access, and the Microsoft Defender stack”
The ad says“Networking good enough to diagnose across the boundary — routing, VLANs, VPN, firewall behaviour. Cisco Meraki and Barracuda experience maps straight onto our stack.”
The ad says“Networking good enough to diagnose across the boundary — routing, VLANs, VPN, firewall behaviour. Cisco Meraki and Barracuda experience maps straight onto our stack.”
The ad says“Azure exposure: virtual machines, networking, backup”
The ad says“Networking good enough to diagnose across the boundary — routing, VLANs, VPN, firewall behaviour. Cisco Meraki and Barracuda experience maps straight onto our stack.”
The ad says“Networking good enough to diagnose across the boundary — routing, VLANs, VPN, firewall behaviour. Cisco Meraki and Barracuda experience maps straight onto our stack.”
The ad says“Windows Server and Active Directory: DNS, DHCP, Group Policy, file services”

The role

You own the problems that do not have an answer written down yet — the multi-system ones, the intermittent ones, the ones where three plausible explanations all fit the evidence.

And then you make them stop happening.

That second half is the part most support roles never get to. Here it is half the job and half of how we measure it. You are not just resolving escalations; you are working out why they keep arriving, and removing the reason.

This is not a senior version of the front line. It is a different job, with a different measure of success: what stops coming to you.

What you will do

Take ownership of escalated incidents — real ownership, not just the next set of hands — and drive them to resolution
Diagnose complex, ambiguous, multi-system problems where the answer is not in any runbook
Raise and drive problem records, eliminating recurring causes rather than repeatedly fixing symptoms
Make the front line better: coaching, shadowing, and writing the runbooks that raise first-line resolution
Hold the line on escalation quality in both directions — coach back what is not ready, and package cleanly what you escalate
Turn the patterns you see into concrete automation proposals for our Architect
Execute change within established customer standards, safely and with rollback in mind
Take part in the second-line on-call rotation

What you bring

Technical

Two or more years supporting Microsoft environments, ideally across multiple customers in a managed services setting
Solid Microsoft 365 administration, including Entra ID — groups, licensing, authentication
Windows Server and Active Directory: DNS, DHCP, Group Policy, file services
Endpoint management with Intune: policy, compliance, application deployment
Practical security: MFA, Conditional Access, and the Microsoft Defender stack
Networking good enough to diagnose across the boundary — routing, VLANs, VPN, firewall behaviour. Cisco Meraki and Barracuda experience maps straight onto our stack.
Azure exposure: virtual machines, networking, backup
Certifications are supported and funded. What you can actually do matters more.

How you work

Structured diagnosis. You form and eliminate hypotheses rather than trying things, and you can explain why the fix worked.
Comfort with ambiguity. The defining feature of this work is that the answer is not documented anywhere.
Pattern recognition. You see the third instance of something and recognize it as the third.
A coaching instinct. You would rather teach someone than take the ticket off them. This is the hardest thing for us to hire and the most valuable thing you can bring.
Risk judgement. You know when to stop, when to escalate, and when to refuse to proceed.

Where it goes

Three capability bands inside the tier, with compensation attached, so growing here does not require leaving here.

Beyond that, four genuine lanes: escalation depth toward Senior Engineer and eventually Architect; implementation and project delivery; automation and platform; or leadership. We will ask you which one you want rather than pointing you at whichever gap hurts us most. You will have a one-page development plan, a monthly conversation, a quarterly capability review, and protected development time.

What we offer

Salary range: $60,000 – $80,000
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
Work. Life. Balance.

About Third Octet

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.

How we screen

We use automated tools to help sort and shortlist applications. Every candidate who reaches the shortlist is reviewed by a person before any decision is made.

This posting is for an existing vacancy.