Strategy Principal, Office of the COO
Core
Strategy and operations partner to the COO and CPO, driving decision-making, market sizing, and execution for embedded insurance growth in Canada and the US.
Role type
Principal Strategy / Chief of Staff
Builds
Strategic recommendations, business cases, executive decks, and an AI operating system (agents, workflows, Claude Skills)
Domain
Fintech / Embedded Insurance / Financial Services
Required skills
Strategy consulting, financial modeling, AI agent building, structured decision-making, B2B enterprise sales, financial services fluency
Preferred skills
Embedded insurance experience, US market exposure, engineering/CS background
Technologies
Claude (Skills, Code, Cowork, Design, MCP), Granola, HubSpot, Apollo.io, Slack, Google Workspace, Microsoft 365, Figma, Lovable, Lucid, Shortcut, Xero
Responsibilities
Run weekly strategic reviews, decide on initiatives within guardrails, manage follow-through on executive decisions, build business cases for enterprise deals, create executive materials, maintain the roadmap and partner records, design and run AI agents/workflows
Seniority
Senior, hands-on IC