Senior IT Support Analyst

Third OctetMississauga, ON
CA$60,000 - CA$80,000Hybrid

About The Position

This role is for a Senior IT Support Analyst who will own and resolve complex, ambiguous, and multi-system problems that do not have readily available solutions. The primary focus is not just on resolving escalated incidents but also on identifying and eliminating the root causes of recurring issues. This position is distinct from frontline support, with success measured by the reduction in escalations. The analyst will also contribute to improving frontline support by coaching, shadowing, and creating documentation, and will be responsible for managing escalations effectively, both receiving and passing them on.

Requirements

  • 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 knowledge: MFA, Conditional Access, and the Microsoft Defender stack.
  • Networking skills sufficient for cross-boundary diagnosis: routing, VLANs, VPN, firewall behavior.
  • Azure exposure: virtual machines, networking, backup.
  • Structured diagnosis approach, forming and eliminating hypotheses.
  • Comfort with ambiguity and undocumented problems.
  • Pattern recognition skills to identify recurring issues.
  • A coaching instinct to teach others rather than simply taking over tickets.
  • Risk judgment to know when to stop, escalate, or refuse to proceed.

Nice To Haves

  • Cisco Meraki and Barracuda experience.

Responsibilities

  • Take ownership of escalated incidents and drive them to resolution.
  • Diagnose complex, ambiguous, multi-system problems where solutions are not documented.
  • Raise and drive problem records to eliminate recurring causes.
  • Improve frontline support through coaching, shadowing, and writing runbooks.
  • Maintain escalation quality by coaching back inappropriate escalations and packaging clean escalations for further review.
  • Propose automation solutions to architects based on observed patterns.
  • Execute change within established customer standards, ensuring safety and rollback capability.
  • Participate in the second-line on-call rotation.

Benefits

  • Personally tailored benefits - health, vision, dental, and paramedical
  • Flexibility in how, when, and where you work
  • 4.5-day workweek
  • 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
  • Leadership that serves your best interest
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