Who we are

InsureLine is one of Canada's fastest-growing insurance brokerage networks, with 50+ locations spanning British Columbia, Alberta, Saskatchewan, Manitoba, and Ontario. We empower our network of independent brokerages with operational growth strategies, business succession planning, industry-leading technology, engaging marketing, and access to Canada's leading insurance markets. As an organization, InsureLine is still young and entrepreneurial — we move fast, and we hold ourselves to a high bar.

Our vision is simple: providing simple insurance solutions to Canadians. Our mission is to give our clients insurance buying choice through a simple, elegant experience powered by sophisticated technology. And we live by three core values — Own It, Innovate, Have Fun — that shape how we work and who we hire.

The opportunity

InsureLine is looking for a Director of Technology to own the outcomes of our entire technology function — not just keep it running. This is a strategic, hands-on leadership role for someone who can operate at the executive table today and grow into our Chief Technology Officer as the role's scope and impact expand.

You will be accountable for the performance, security, and business value of every system, application, and managed service InsureLine runs — and for the people who build and support them. You'll set the technology agenda alongside the President and executive leadership, translate business priorities into a technology roadmap, and be the person this organization looks to when a critical system, vendor relationship, or security incident needs a decisive owner.

We're not looking for someone to run the playbook we already have. We're looking for someone who's plugged into where technology is actually headed, who reads the room and says "there's a better way to do this," and who's genuinely energized by figuring out what that better way looks like — then building it.

This role leads three teams — Systems, Infrastructure & Security, and Software Development — and a growing technology department as InsureLine's network continues to grow.

One thing to be direct about: this is not a purely strategic seat. Our President and CEO both conceptualize, plan, and execute — we're willing to sweep the floor if that's what the day requires — and we're looking for the same instinct in this role. You'll set the vision and lead the team, but you also need to be able to get into the weeds yourself: troubleshoot the system when it's down, review the code when it matters, and pick up the work directly when the situation calls for it, not just direct someone else to.

What you'll ownTechnology strategy & vision

- Set and own InsureLine's technology roadmap, aligning investment in systems, infrastructure, and applications with business growth targets
- Bring an outside perspective — new tools, new approaches, ideas pulled from outside the insurance industry — and challenge how we've always done things when there's a genuinely better way
- Represent technology at the leadership table — translating business priorities into technology decisions, and technology trade-offs into business terms
- Identify where AI and automation can meaningfully improve InsureLine's operations, and lead the evaluation, piloting, and adoption of tools that deliver real efficiency gains
- Build the technology department's operating model, budget, and reporting cadence as the organization scales

Organizational & people leadership

- Own the performance, growth, and structure of a multi-team technology department, building the org design, career paths, and accountability needed as headcount grows
- Build and develop a leadership bench within the department — team leads and managers capable of eventually taking on more of what you own today




- Be accountable for the department's results, not just its delivery — the standard is business impact, not activity

Business applications & data

- Own the outcomes of InsureLine's broker management system (BMS) strategy, including vendor evaluation, selection, and implementation as the network's needs evolve
- Ensure the systems and applications serving the InsureLine Network deliver measurable value to 50+ franchise locations — not just uptime
- Own the roadmap for reporting, data, and business intelligence, so leadership and franchise stakeholders can trust the numbers driving their decisions
- Oversee InsureLine's data lake and business intelligence reporting infrastructure, ensuring data from across the network is structured, governed, and usable for decision-making

Infrastructure, security & managed services

- Own the security and reliability of InsureLine's technology footprint — infrastructure, cloud, endpoints, and the managed services program delivered across every location in the network
- Ensure the managed services program continues to meet the standards required by InsureLine's cyber insurance carriers, and evolve it as the network and threat landscape grow
- Set the standard for incident response, vendor and tooling selection, and service delivery across a distributed, 50+ location network

Software development & innovation

- Own the outcomes of InsureLine's custom application and software development function, ensuring what gets built is prioritized against real business impact
- Bring direct experience managing a software development or engineering function — you don't need to write the code, but you need to know how to run the team that does

Vendor & procurement leadership

- Own major technology vendor relationships and procurement from business case through contract to renewal, including RFPs, negotiations, and ongoing accountability
- Act as the executive owner of vendor performance across the department — if a vendor isn't delivering, that call belongs to you

What success looks like in year one

- You're the recognized subject matter expert on InsureLine's technology — not just administering it, but understood by leadership as the person who truly knows how it all fits together
- Technology costs and budgeting are fully under your control, with a clear, defensible cost model across the department and no surprises heading into the following year
- You've built a clear, resourced staffing plan tied to the network's growth trajectory — you know what roles you'll need, when, and why
- The technology department runs on transparent KPIs, a defined reporting cadence to the President, and a documented org structure
- The managed services program has been reviewed and optimized for the network's current scale
- The technology function has passed its most recent cyber insurance security review without material findings, with a documented plan for anything still open
- Major vendor contracts (BMS, managed services tooling, cloud) have been reviewed for value and terms, with at least one meaningful renegotiation or consolidation completed
- Franchise locations report a measurable improvement in their experience with technology support and the managed services program
- At least one AI or automation initiative has delivered a noticeable, measurable business impact — not just a pilot, but something the business can point to




- You've established credibility as a leadership-table voice on technology — not just an operator

What you bringRequired

- 7+ years of progressive technology experience, with real ownership of technical teams or departments — whether your title today is Manager, Senior Manager, or Director
- Direct experience managing a software development or custom applications function — you've led developers, not just consumed their output
- Direct experience with a managed services model, either delivering one or owning it from the client side
- Demonstrated breadth across infrastructure, cyber security, and business applications — deep expertise everywhere isn't required, but real fluency in each is
- Working knowledge of AI and automation tools and where they create genuine business value in a technology organization
- Experience owning vendor relationships and major procurement processes (RFPs, contract negotiation, implementation oversight)
- A track record of building and scaling technology teams and org structures as a company grows
- A genuine willingness to be hands-on — comfortable doing the work yourself when the situation calls for it, not just directing others to do it
- Executive-level communication skills — comfortable setting the technology agenda with a president, CEO, or board

Preferred

- Experience in insurance, financial services, or another regulated, multi-location network business
- Experience supporting franchise operations, or another multi-site, semi-autonomous business model
- Experience with broker management systems or other vertical-specific business platforms
- Experience with multi-cloud environments (Microsoft 365 / Azure, AWS, GCP, private cloud) — we're a cloud-first organization

The path forward

This is a high-autonomy, high-visibility role with a clear, demonstrated path to Chief Technology Officer as InsureLine's network and technology footprint continue to grow. Compensation reflects that trajectory and will be discussed based on the experience you bring.

Ready to build this with us?

If you read this and started mentally rewriting our roadmap before you even finished — good. That's the reaction we're hoping for. Send us your resume, and tell us about a time you challenged how something was "always done" and made it better. We'd love to hear it.

Pay: $125,000.00-$150,000.00 per year

Benefits:

- Dental care
- Extended health care
- Paid time off
- RRSP match

Application question(s):

- How many years of progressive technology leadership experience do you have, including direct management of technical teams or departments?
- Have you directly managed a software development or custom applications team?
- Do you have direct experience with a managed services (MSP) model — either delivering one, or owning the relationship from the client side?
- Which of the following do you have hands-on experience in? (Select all that apply: IT infrastructure/networking · cyber security · business applications/systems · software development)
- Have you led a major technology vendor procurement process — RFP, evaluation, contract negotiation, and implementation?
- This role is hands-on as well as strategic — are you comfortable personally troubleshooting a system, reviewing code, or doing the work yourself when the situation calls for it, not just directing others?
- Do you have experience working with AI or automation tools in a way that delivered a measurable business outcome, not just a pilot or trial?
- Do you have experience with multi-cloud environments (e.g., Microsoft 365/Azure, AWS, GCP, private cloud)?
- This role is hybrid, based out of our Port Coquitlam, BC head office, with occasional travel to other InsureLine locations across BC, AB, SK, MB, and ON. Are you able to work under this arrangement?

Work Location: Hybrid remote in Port Coquitlam, BC V3C 6N2

📌 Director of Technology (Canada)
🏢 InsureLine Brokers Inc. (Head Office)
📍 Canada