Position Title: Head of AI
Location: Toronto, ON (Hybrid)
Reporting To: Chief Technology Officer
Employment Type: Full-Time
About the Company
We are recruiting on behalf of a fast-growing, venture-backed technology platform specializing in AI orchestration for the Property & Casualty (P&C) insurance sector. By helping commercial insurers source, integrate, and build specialized AI solutions, the platform streamlines complex underwriting, claims processing, and policy servicing workflows. The company is led by an experienced leadership team and supported by prominent industry advisors, including former executives from top-tier global insurance brokerages, leading digital insurtechs, and major private equity firms.
Position Overview & Key Responsibilities
The Head of AI will own the overarching technical and strategic direction of the AI orchestration platform. This is a hands-on "player-manager" leadership role bridging high-level platform strategy with direct technical execution.
Strategic Leadership: Own the AI roadmap reporting directly to the CTO. Lead critical build-vs-partner evaluations, set rigorous model governance and explainability standards, and scale the AI/ML engineering and data science teams.
Technical Direction: Drive hands-on platform evolution on AWS, transitioning core connections toward advanced Agent-to-Agent architectures and Model Context Protocol (MCP) frameworks.
Stakeholder & Client Engagement: Serve as the primary technical authority on AI capabilities in high-stakes discussions with enterprise insurance clients, strategic partners, and the executive board.
Target Profile & Qualifications
8+ years of progressive AI/ML experience with a strong foundation in software/data engineering rather than pure research.
Proven track record of deploying production-grade AI systems into complex, regulated enterprise environments (Financial Services, Insurance, or Fintech).
Hands-on familiarity with agentic workflows, LLM orchestration, Model Context Protocol (MCP), and AWS infrastructure.
Strong executive communication skills—equally effective coding alongside engineers, aligning with the CTO, or presenting to client executives.
Prior experience spanning both established enterprise environments and fast-paced startup/scale-up settings.
Compensation & Perks
Competitive base salary plus an equity package.
5 weeks of paid vacation and flexible hybrid working arrangements (Toronto office base).
Head of AI • Toronto, ON, Canada
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