Senior Infrastructure & Security Analyst
Who We Are
InsureLine is one of Canada's fastest-growing insurance brokerages, with 45+ offices from coast to coast. Behind every branch is a technology backbone that has to be fast, secure, and dependable — and that's where you come in. We're growing our technology team and looking for someone who loves solving hard problems, making systems better, and helping people do their best work.
About the Role
As our Senior Infrastructure & Security Analyst, you'll be the go-to expert who keeps our people productive and our infrastructure resilient. You'll blend hands-on technical depth with a builder's mindset — resolving the toughest escalations one moment and designing smarter, more automated, more secure systems the next. It's equal parts trusted advisor, mentor, and hands-on engineer, with real room to shape how we work.
What You'll Do
· Be the senior escalation point for the support team — untangling complex, cross-system incidents and driving them to resolution alongside internal teams and vendors.
· Deliver responsive, genuinely helpful support to colleagues across 45+ locations, owning each issue end to end and keeping people informed on progress, risks, and next steps.
· Run and continually sharpen our Microsoft 365 environment — identity, email, collaboration, security, and device management — with an eye for governance and standardization.
· Keep our Azure environment (including Azure Virtual Desktop / Cloud PCs) reliable, secure, performant, and cost-aware.
· Maintain and improve corporate networking — internet, WiFi, LAN/WAN, VPN, routing and switching — plus the end-user devices that connect to it, pushing for better uptime and cleaner standard configurations.
· Support the business applications that live outside M365, managing integrations, vendor relationships, and day-to-day operational health.
· Own and level up our security posture: endpoint and email protection, identity controls, vulnerability reduction, incident response, and security-awareness enablement.
· Lead small-to-mid-sized initiatives and contribute to bigger projects — scoping requirements, timelines, risks, and change impacts, then coordinating testing and rollout.
· Team up with the Systems Team to raise the bar on architecture and operational maturity — standard builds, backup/DR readiness, patching cadence, access models, segmentation, and automation.
· Write and maintain documentation, knowledge-base articles, and technical standards that make solutions repeatable and easy to support.
· Track the metrics that matter — support, reliability, and security — spot the trends, and turn them into real improvements.
· Refine how we deliver service: ticket quality, prioritization, escalation paths, SLAs/OLAs, and root-cause analysis.
· Mentor and coach teammates through pairing, knowledge sharing, and honest feedback, helping build a collaborative, high-accountability culture.
· Translate the technical into the practical for non-technical stakeholders — setting expectations, documenting decisions, and making clear, actionable recommendations.
What You Bring
· A track record in a senior technical support or systems role — and the ownership mindset that comes with it.
· Excellent communication: you make complex topics make sense to anyone, set expectations, and document decisions cleanly.
· A natural collaborator who partners easily across support, systems, and security, and with business leaders, vendors, and third parties.
· Leadership instincts — you've coached others, run knowledge-sharing sessions, improved team consistency, and been the person people escalate to.
· Delivery chops — scoping and shipping small projects and initiatives, juggling priorities, and managing risk and change.
· An architect's eye — you assess current-state infrastructure, recommend pragmatic improvements, standardize configurations, and automate for reliability and security.
· Deep Microsoft 365 administration experience (client and cloud), including backups and operational governance.
· Microsoft Entra experience for device and user management (Entra ID and related tooling).
· Azure administration experience, including Azure Virtual Desktop (AVD) configuration and management.
· Solid endpoint and device support — desktop support plus iOS/Android setup and Outlook email configuration.
· Strong networking fundamentals — topology, routers, switches, TCP/IP, LAN/WAN, and connectivity troubleshooting.
· Hands-on experience with a PSA/ticketing platform (ConnectWise, FreshDesk, Autotask, or similar), with a bias for clean notes, categorization, and escalation.
· RMM/endpoint management experience (SuperOps, NinjaRMM, ConnectWise, or similar).
· PowerShell and scripting experience, plus comfort with APIs to reduce toil and improve consistency.
· Power Platform experience (Power Apps and Power Automate) — or the drive to learn and apply it.
· Endpoint security tooling experience (Defender, Huntress, Zorus/DNSFilter, or similar).
· Email security gateway experience (Defender for Office 365, Proofpoint, Mimecast, or similar).
· Security-awareness platform experience (Beauceron, KnowBe4, Huntress, or similar).
· Cloud backup experience (Datto or similar).
· A genuine grasp of IT security best practices, and a strong sense of ownership and accountability.
Nice to Haves
· Linux and AWS experience.
· VoIP experience.
What's In It For You
· Competitive salary of $80,000–$100,000, based on your skills and experience.
· Dental care.
· Employee Assistance Program.
· RRSP Employee Program.
· Hybrid flexibility so you can do your best work from the office and from home.
The Details
· Job type: Full-time.
· Schedule: Monday to Friday, with occasional weekends as needed.
· Location: Hybrid — Port Coquitlam, BC or Calgary, AB.
· Experience we're looking for: Microsoft 365, Azure, desktop support, help desk, and network support (5 years each, required); leadership or management experience is a plus.
Life at InsureLine
We're a group of people united by a genuine desire to serve. We know the difference our team makes in building a workplace that's inclusive, innovative, and welcoming — one where everyone belongs. That's why we're intentional about who we bring on board: talented people who pair real skill with a genuine drive to help others succeed. If that sounds like you, we'd love to hear from you.
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: Hybrid remote in Port Coquitlam, BC
