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Added 27 mins ago
TD
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TEEMA

Service Desk - System & Security Tier 2

Calgary, AB, Canada

Full-time

Apply About employer

Applications open in a new tab.

Job details

Job type: Full-time
Apply by: Nov 27, 2026
Experience: 4+ years hands-on IT experience, ideally in an MSP or multi-client environment
Posting language: English
Posted: Oct 28, 2026

Original job description

Tier 2 Technician

Systems & Security | Managed Services

Location: Calgary, AB - hybrid/remote, occasional onsite and client-facing

Type: Full-time, permanent

About the Opportunity

Our client is a well-established Calgary-based managed services provider with a cybersecurity-first focus, supporting regulated businesses across legal, finance, oil and gas, medical and non-profit sectors.

This is a small, owner-operated shop. There are no layers, no ticket-number anonymity, and no waiting weeks for a decision. Everyone touches real work and the person in this seat has visible impact from week one.

They have also moved harder and faster on AI and automation than most providers in this market, and are actively building it into how the business delivers service. If you are already using AI in your day-to-day work rather than reading about it, this is a rare place to do more of that.

The Role

A hands-on Tier 2 seat working under the service delivery lead. The work is escalations off the frontline, bounded project delivery, security control implementation and regular onsite client work. You will not be the sole expert in every domain, and you are not expected to be - but you will own what lands on your desk through to a verified finish.

What You Will Do

Own escalations that come off the frontline through to verified resolution
Administer and troubleshoot Microsoft 365 across multiple client tenants - Exchange Online, Teams, SharePoint, OneDrive, licensing, mailboxes, groups and permissions
Work in Entra ID on sign-in, authentication, MFA and identity lifecycle issues
Diagnose and remediate Windows endpoint, application and peripheral problems; deploy and configure through Intune
Support Windows Server, Active Directory and virtualization
Troubleshoot VPN, Wi-Fi, switching, DNS, DHCP and firewall connectivity
Deliver defined projects - client onboardings, migrations, workstation deployment waves, network and server changes - including testing, verification and handoff
Implement approved security controls, handle phishing and EDR alerts, gather evidence and verify remediation
Perform onsite assessments, installations and follow-up across the Calgary service area
Use approved AI tooling in daily work and help turn recurring fixes into better documentation and safe automation

What We Are Looking For

4+ years hands-on IT experience, ideally in an MSP or multi-client environment
Daily working knowledge of Microsoft 365 administration
Entra ID / Azure AD, Windows endpoints, Intune, Windows Server and Active Directory
Practical networking - VPN, Wi-Fi, DNS, DHCP, firewalls
Experience with an RMM and a PSA in production, with clean ticket, time and work records
Practical security judgment - implementing controls, handling alerts, completing remediation within your authority
Comfortable owning your own queue and prioritizing without being chased
Strong communication - you update people before they have to ask
Able to sit in front of a client and explain a problem in plain language
Valid driver's licence and reliable transportation
Eligible to work in Canada

The AI Piece

This matters more here than almost anywhere else in the Calgary market, and it is worth being specific about what the client is actually after.

They are not looking for an AI engineer or someone who will build their platform. They are looking for a technician who already uses AI as part of how they work - for scripting, documentation, troubleshooting, or turning repeat problems into automation - and who exercises judgment about where it belongs and where it does not.

If you validate what it gives you, understand what data should never go near it, and can point to something you have actually built or improved with it, that will carry real weight. Enthusiasm without evidence will not; neither will resistance.

Nice to Have

Datto, N-able, Autotask, ConnectWise, IT Glue, Sophos, Defender, Ubiquiti, Fortinet, Meraki, 3CX, PowerShell, Microsoft or CompTIA certifications.

Comparable platforms are fine. Our client will train on their specific stack - they care more about judgment, ownership and follow-through than product acronyms.

Who Does Well Here

Someone from a smaller shop who is used to wearing several hats and does not want to be siloed. You drop your own project when a client is down. You close the loop, document as you go, and finish the last ten percent. You ask for help when you need it rather than disappearing into a problem. You are open to new technology rather than dug in.

This role will not suit someone looking for remote-only work, avoiding client contact, or wanting to move away from hands-on delivery.

What Is on Offer

Permanent role with a stable, growing provider
Direct access to ownership and fast decisions
Three weeks vacation
Supported training and certification
Broad exposure across cloud, security, networking, voice and projects
Genuine room to grow as the team builds out

Apply About employer

More about this job

Responsibilities

Own Tier 2 escalations through verified resolution, administer Microsoft 365 and identity services, troubleshoot endpoints, servers, and networks, and deliver defined client projects. Implement approved security controls, respond to alerts, perform onsite client work, and use AI tools to improve documentation and safe automation.

Requirements

Candidates need at least four years of hands-on IT experience, preferably in an MSP or multi-client environment, with working knowledge of Microsoft 365, Entra ID, Windows, Intune, servers, Active Directory, and practical networking. They should have production experience with RMM and PSA tools, sound security judgment, strong ownership and communication skills, a valid driver's licence and reliable transportation, and eligibility to work in Canada.

Skills

Microsoft 365 Administration
Entra ID
Intune
Windows Server
Active Directory
Networking
VPN Troubleshooting
DNS And DHCP
Endpoint Troubleshooting
Security Controls
Incident Remediation
Project Delivery
RMM And PSA Tools
Client Communication
AI-Assisted Automation
PowerShell

Benefits

Three Weeks Vacation
Supported Training And Certification
Career Growth Opportunities

Visa sponsorship

Not detected in the job text

Keywords

Managed Services Provider
Cybersecurity
Microsoft 365
Exchange Online
Microsoft Teams
SharePoint
OneDrive
Entra ID
Azure AD
Multi-Factor Authentication
Intune
Windows Server
Active Directory
Virtualization
VPN
Wi-Fi
Switching
DNS
DHCP
Firewalls
RMM
PSA
Datto
N-able
Autotask
ConnectWise
IT Glue
Sophos
Microsoft Defender
Ubiquiti

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