Job description: Senior Technical Support Analyst
InsureLine is a leading insurance franchise brokerage with 45+ locations across Canada. We’re expanding the support team and are seeking a Senior Technical Support Analyst - Tier 3 who combines deep hands‑on technical capability with leadership, strong communication, and a continuous‑improvement mindset.
In this role, you’ll provide expert end‑user and systems support while helping evolve and strengthen the architecture of our IT infrastructure through standardization, security improvements, automation, and practical roadmaps.
Key Responsibilities: Provide timely, professional, customer‑focused technical support to staff across multiple locations; own issues through resolution and communicate clearly on progress, risks, and next steps.
Serve as a senior escalation point for the technical support team, troubleshooting complex incidents and coordinating resolution across internal teams and vendors.
Administer, support, and continuously improve the Microsoft 365 setting (identity, email, collaboration, security, and device management), including operational governance and standardization.
Support and optimize the corporate Azure environment (including Azure Virtual Desktop / Cloud PCs where applicable), focusing on reliability, security, performance, and cost awareness.
Support and maintain corporate networking (internet, Wi‑Fi, LAN/WAN, VPN, routing/switching) and end‑user devices; drive improvements to availability, standard configurations, and monitoring.
Support and maintain business applications outside of Microsoft 365; manage integrations, vendor coordination, and operational health as required.
Own and enhance IT security practices: endpoint protection, email security, identity controls, vulnerability reduction, incident response support, and security awareness enablement.
Lead small‑to‑medium initiatives and contribute to larger projects by defining scope, requirements, timelines, risks, and change impacts; coordinate testing and rollout plans.
Partner with the Systems Team to improve infrastructure architecture and operational maturity (e.g., standard builds, backup/DR readiness, patching cadence, access models, segmentation, and automation).
Create, maintain, and enforce explicit internal documentation, knowledge base articles, and technical standards; ensure solutions are supportable and repeatable.
Track and report on support, reliability, and security metrics (monthly/quarterly/annually); identify trends and translate findings into actionable improvements.




Improve service delivery by refining processes (ticket quality, prioritization, escalation paths, SLAs/OLAs, and root‑cause analysis) and promoting best practices.
Mentor and coach team members through knowledge sharing, pairing on complex tickets, technical guidance, and constructive feedback; help build a collaborative, high‑accountability support culture.
Communicate effectively with non‑technical stakeholders, including setting expectations, documenting decisions, and presenting recommendations in a clear, practical way.
Required Skills and Experience: Senior‑level communication: strong written and verbal communication; able to translate technical topics for non‑technical audiences, set expectations, and document decisions clearly.
Collaboration & stakeholder management: proven ability to partner across IT (support/systems/security) and with business leaders, vendors, and third parties to drive outcomes.
Leadership & mentoring: experience coaching others, running knowledge‑sharing sessions, improving team consistency, and serving as an escalation resource.
Planning & delivery: experience scoping and delivering small projects/initiatives, managing priorities, risks, change impacts, and rollout plans.
Architecture & continuous improvement mindset: ability to assess current‑state infrastructure, recommend pragmatic improvements, standardize configurations, and increase reliability/security through repeatable practices and automation.
Microsoft 365 administration: strong experience across the M365 ecosystem (client and cloud administration), including backups and operational governance.
Microsoft Entra experience: device and user management experience (Entra ID and related tooling).
Azure experience: supporting and administering Azure services; Azure Virtual Desktop (AVD) configuration and management experience.
Endpoint & device support: desktop support experience plus iOS/Android device setup and Outlook email configuration.
Networking fundamentals: strong understanding of network topology including routers, switches, TCP/IP, LAN/WAN, and troubleshooting connectivity issues.
Ticketing/PSA tools: experience with a PSA/ticketing system (ConnectWise, FreshDesk,



Autotask, or similar) with emphasis on high‑quality ticket notes, categorization, and escalation.
Endpoint management / RMM: experience with RMM/endpoint management tooling (SuperOps, NinjaRMM, ConnectWise, or similar).
Scripting & automation: PowerShell and scripting experience; comfort working with APIs to reduce toil and improve consistency.
Power Platform: experience with Power Apps and Power Automate (or demonstrated ability to learn and apply automation tools).
Security tooling: endpoint security configuration/management experience (Defender, Huntress, Zorus/DNSFilter, or similar).
Email security: email security gateway configuration/management experience (Defender for Office 365, Proofpoint, Mimecast, or similar).
Security awareness: configuration/management experience with security awareness training platforms (Beauceron, KnowBe4, Huntress, or similar).
Backup solutions: cloud backup experience (Datto or similar).
Linux and AWS experience (desired but not required).
VoIP experience (desired but not required).
Understanding of IT security best practices and a strong sense of ownership and accountability.
Previous experience in a similar senior technical support / systems support role.
At InsureLine, we are a collection of people who share the inherent desire to serve. We recognize the profound impact our people have in fostering a work environment that is inclusive, innovative and ensures a sense of belonging for all. As such, we are intentional and self‑reflective about the team we are building by seeking talented individuals who bring both incredible skills and a desire to support the success of others.
Job Type: Full‑time
Benefits: Dental care
Employee assistance program
RRSP Employee Program
Schedule: Monday to Friday
Weekends as needed
Experience: Microsoft 365: 5 years (required)
Azure: 5 years (required)
Desktop support: 5 years (required)
Help desk: 5 years (required)
Network support: 5 years (required)
Leadership or Management Experience (desired)
Work Location: Hybrid remote in Port Coquitlam, BC or Calgary AB
Salary : between $80,000 - $100,000
Job Type: Full‑time
Pay: $80,000.00-$100,000.00 per year
Benefits: Casual dress
Dental care
Paid time off
RRSP match
Work from home
Experience: Similar Role : 5 years (required)
team lead: 3 years (required)
MSP (managed service provider): 3 years (required)
Language: Fluent and clear English (required)
Work Location: In person

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