Engineering Manager, Core Product Engine (Backend)

TL;DR

Engineering Manager, Core Product Engine (Backend): Evolve automation systems orchestrating complex multi-step insurance transactions with external systems with an accent on asynchronous state management, real-time reliability, and fault-tolerant frameworks. Focus on refactoring legacy tightly-coupled logic into scalable architecture and building AI-first internal tools for growth from 5M to 50M users.

Location: Remote from Toronto, Hamilton, Kingston, London, Markham, Ottawa, or Waterloo, Ontario (Canada)

Salary: CA$230K–CA$280K + equity

Company

America’s first super app simplifying car ownership including insurance marketplace, maintenance, and more powered by AI/ML with 5M+ customers.

What you will do

• Lead incremental refactoring of existing automation systems, designing new standards for predictability and testability while pairing with engineers.
• Deep dive into technical and business logic of core insurance product to handle provider-specific behaviors.
• Evolve systems to robust framework handling external changes gracefully and scaling to new categories.
• Shift to AI-first approach for next-gen internal tools supporting massive user growth.
• Spend 80% time hands-on technical work like architecture transitions.

Requirements

• Remote from specified Ontario cities (Toronto, Hamilton, Kingston, London, Markham, Ottawa, Waterloo).
• Player coach with founder or lead architect experience at early-stage startup.
• Obsessed with success rates, hunting edge cases in complex business logic.
• Systems thinker excelling in design for offline asynchronous jobs, decoupling, state management, retry logic.
• Hands-on builder reporting to CTO.

Nice to have

• Experience with insurance domain complexity.

Culture & Benefits

• Direct ownership with CTO involvement, no bureaucracy—pitch, build, deploy in days.
• Small high-bar team of passionate ex-founders moving fast.
• Comprehensive benefits: health/dental/vision, PTO, parental leave, RRSP matching (Canada), wellness.
• Equity opportunities.
• Access to massive customer data for decisions.