A Vancouver-based startup applying AI to the insurance industry is scaling its engineering organization. The company is well funded by North American investors and has been recognized among Canada's fastest-growing tech companies. It builds vertically-focused AI products for insurance agencies and brokerages, combining deep domain expertise with proprietary models to automate real operational workflows.The Role
This is an engineering leadership position overseeing two teams focused on agentic workflows and natural language product experiences. You will report to the VP of Engineering and sit on the engineering leadership team, owning delivery against a multi‑quarter roadmap while building the processes, standards, and culture that let the org scale with headcount. The ideal candidate has run engineering teams before, is comfortable operating in ambiguity, and wants a hands‑on leadership role in a growing AI company.What You Will Do
Lead two engineering teams building agentic workflows and natural language product featuresSet the multi‑quarter roadmap and drive delivery against scalability and reliability goalsHire,



coach, and mentor engineers, building a robust cross‑functional teamSet technical direction and raise the bar on engineering practices across the product lifecyclePartner closely with product, data/AI engineering, and customer‑facing teams to align prioritiesWhat You Bring
4+ years managing engineering teams8+ years of overall skilled engineering experience5+ years delivering mission‑critical software in productionStrong grounding in the full SDLC, including code review, testing, and release practices at scaleExperience designing databases, backends, and APIs, with a track record of operating software in productionWhy This Role
This is a chance to lead engineering for the parts of the product driving the company's growth, with direct access to leadership and real input into how the org scales. The team builds AI‑first, working on problems with immediate, measurable business impact rather than incremental feature work.
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📌 Director Of Engineering Winnipeg
🏢 TekRek
📍 Winnipeg