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
