Job description: Senior Technical Support AnalystInsureLine is a leading insurance franchise brokerage with 45+ locations across Canada. We’re expanding our 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 environment (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 clear 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 co