Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
Product Marketing Manager
Date Posted
May 12, 2026
Full Job Description
đź“‹ Description
- • As Tech Lead, Core Product Engine (Backend) at Jerry Technologies Inc., you will lead the evolution of the company’s critical automation systems that power the end-to-end insurance shopping experience for over 5 million customers, transforming a legacy, tightly coupled system into a robust, fault-tolerant, and scalable framework capable of supporting growth to 50M users.
- • Day to day, you will spend 80% of your time in hands-on technical work, including refactoring legacy automation systems, designing new standards for decoupled architecture, pairing with engineers to ensure testability and predictability, and leading the transition toward an AI-first approach for internal tools that enable scalable product innovation.
- • You will join a small but mighty team of high-caliber engineers reporting directly to the co-founder/CTO, where ownership is paramount, red tape is minimal, and ideas move from pitch to production in days — working alongside ex-founders who thrive on solving complex, real-world problems.
- • In this role, you will deepen your expertise in asynchronous state management, real-time system reliability, and complex business logic orchestration across external systems, while gaining exposure to massive consumer data sets (driving, telematics, payment, shopping) and shaping the technical foundation for Jerry.ai’s next-generation super app.
🎯 Requirements
- • Proven experience as a lead architect or founder at an early-stage startup, with a builder’s mindset and comfort working hands-on in the trenches alongside engineering teams.
- • Deep expertise in system design for offline, asynchronous jobs, including strong proficiency in decoupling, state management, failure retry logic, and handling external interface changes with resilience.
- • Strong proficiency in TypeScript and Nest.js, with practical experience building and scaling backend services on AWS (ECS/EKS, Lambda) and working with GraphQL APIs.
- • Exceptional analytical and debugging skills — you are obsessed with success rates and relentlessly pursue root causes of failures in complex business logic, especially across heterogeneous external systems.
- • Ability to lead incremental refactoring efforts while maintaining system stability, balancing technical debt reduction with business continuity and team collaboration.
🏖️ 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 total compensation, aligned with company growth and long-term value creation.
- • Wellness benefits and access to resources supporting physical and mental well-being.
- • Direct access to leadership and a high-autonomy environment where ideas can be implemented rapidly without bureaucratic delays.
- • Exposure to a massive scale of real-world consumer data (5M+ customers) and the chance to work on AI-driven internal tools that will scale the platform to 50M users.
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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