Engineering Team Lead, Core Product Engine (Backend)

Jerry Technologies Inc.

Job Overview

Location

Toronto, Ontario

Job Type

Full-time

Full Job Description

📋 Description

• As Engineering Team Lead for the Core Product Engine (Backend), you will own the critical "last mile" of Jerry.ai's insurance marketplace, orchestrating complex, multi-step transactions with external systems to finalize policy purchases in a high-stakes environment where modern APIs are lacking.
• You will spend 80% of your time in hands-on technical work, leading the evolution of legacy automation systems into a robust, fault-tolerant, and scalable framework capable of handling external interface changes and scaling across dozens of new categories with minimal manual intervention.
• You will join a small, high-caliber team of builders and ex-founders who move fast, report directly to the co-founder/CTO, and operate with minimal bureaucracy — enabling rapid iteration from idea to production in days.
• You will gain deep expertise in insurance domain complexity, lead architectural refactoring, and later drive an AI-first approach to internal tools that will support scaling from 5M to 50M users, all while working with massive customer data streams from telematics, payments, and shopping behaviors.

🎯 Requirements

• Proven experience as a founder, lead architect, or technical leader in an early-stage startup environment with a builder mindset and comfort working in the trenches alongside your team.
• Deep expertise in system design for offline, asynchronous jobs, with strong standards for decoupling, state management, and failure retry logic — particularly in complex, high-reliability backend systems.
• Proficiency in TypeScript and experience with Nest.js, GraphQL, and AWS services (ECS/EKS, Lambda) as part of the current tech stack.
• Obsession with success rates and edge cases — ability to hunt down root causes in complex business logic and ensure predictability and testability in automated systems.

🏖️ Benefits

• Comprehensive benefits package including health, dental, and vision coverage, paid time off, paid parental leave, and a 401(K) plan with employer matching.
• Opportunities for equity grants as part of the total rewards package.
• Access to wellness benefits and other perks designed to support employee well-being.
• Direct access to leadership and the ability to ship impact quickly in a fast-moving, low-bureaucracy environment.

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Jerry Technologies Inc.

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About Jerry Technologies Inc.

Jerry Technologies offers a mobile-first AI platform that automatically compares insurance quotes, refinances auto loans, and shops for home and renters coverage. Users submit photos of existing policies, and the app retrieves and compares rates from carriers to find lower premiums or better terms. The company earns commissions from insurers when policies are switched or originated through its platform, serving consumers seeking to reduce recurring auto and home expenses without manual comparison shopping.

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