IT Support Technician III / System Administrator

The Role

We're hiring an IT Support Technician III in Montréal to act as the senior escalation point for our clinics across the United States. This is a hands-on, queue-driven role: you'll work tickets every day, resolving the problems our 1st and 2nd line technicians can't across Microsoft 365, endpoints, security tooling, telephony, and networking.

One day you might be untangling an Exchange Online mail-flow issue, triaging an EDR alert, rebuilding a clinic's phone tree, and setting up a new site's network. You'll escalate infrastructure, security, and architecture work to our Senior IT Engineer.

Schedule: Monday to Friday, 12:00 – 20:00 Eastern, aligned to our US clinics' business hours. We don't run weekend support, though the team occasionally helps out for urgent issues or planned cutovers.

What you'll do

• Work the escalation queue: This is the core of the job. You'll live in Zendesk: taking escalated tickets from our 1st and 2nd line technicians, driving them to resolution against SLA, and being the last stop before an issue reaches our Senior IT Engineer.

• Microsoft 365 and Entra ID: Exchange Online mail flow, SharePoint and OneDrive permissions, Teams, licensing, MFA and conditional access, and tenant-to-tenant migrations.

• RMM and MDM: Windows and macOS builds, patching, policy, application packaging, remote support, and agent health across the fleet. Printing, scanning and peripherals sit here too.

• Security tooling (AV / EDR): Triage and action endpoint detection alerts, keep agent coverage complete across every device, support phishing simulation and security awareness campaign, and escalate genuine incidents promptly.

• VoIP and telephony: Cloud VoIP administration, IVR and call-flow builds, ring groups, voicemail, number porting, handsets, and call routing across time zones.

• Networking: Diagnose connectivity, wireless, VLAN, VPN, and firewall issues at clinic sites; coordinate with ISPs and escalate hardware faults.

• Clinic onboarding: Once onboarded and have a full understanding of clinic structure you will help with clinic onboardings and standardization.

• Clinical platform support (secondary): Day-to-day account, access, and workstation-side support for our EMR and practice-management systems (Zenoti, Nextech, PatientNow, Dr. Chrono, Meevo) and consultation-room iPads and imaging hardware.

• Documentation and mentoring: Maintain SOPs and knowledge-base articles in Zendesk, keep asset and licence records accurate, and coach the L1/L2 technicians so more issues are solved correctly the first time.

You'll work to our published SLA: 60-minute average first response and 3-business-day resolution on standard tickets; 15-minute response and 4-business-hour restoration on P1 incidents. We care as much about tickets staying closed as about closing them quickly.

What we're looking for

• 5+ years in IT support, including 2+ years at a 3rd-line or senior escalation level. This is a senior role

• Real depth in Microsoft 365 and Entra ID administration

• Strong Windows and macOS troubleshooting, with hands-on RMM and MDM experience managing a fleet.

• Working knowledge of endpoint security tooling — AV / EDR alert triage, agent deployment and coverage.

• Experience administering a cloud VoIP platform, including building call flows or IVRs.

• Solid networking fundamentals: DNS, DHCP, VLANs, VPN, firewall rules, Wi-Fi.

• Comfortable working a ticket queue to SLA in a helpdesk platform such as Zendesk, and documenting as you go.

• Excellent communication — you can explain a technical problem to a non-technical clinician with patience and clarity.

• Comfortable supporting users remotely across multiple sites and time zones, and prioritising against SLA.

• Legally entitled to work in Canada.

Nice to have: experience supporting users across multiple sites or at a managed service provider; Microsoft 365 or Google Workspace tenant migrations; familiarity with HIPAA or another data-protection regime.

Language: Knowledge of English is required, as this role provides direct daily support — verbal and written — to clinic staff located exclusively in the United States, and our clinical, security, and vendor platforms operate in English. French is an asset but is not required for the duties of the role.