Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
Engineering Manager
Date Posted
February 25, 2026
Full Job Description
đź“‹ Description
- • As an Engineering Manager at Jerry Technologies Inc., you will be at the forefront of revolutionizing car ownership by tackling the complex technical challenges within our insurance marketplace automation. This role is designed for a hands-on leader who thrives in a fast-paced, ownership-driven environment, reporting directly to our co-founder/CTO. You will be instrumental in evolving our current automation systems into a robust, fault-tolerant framework capable of scaling to handle dozens of new categories with minimal manual intervention.
- • The core of your challenge lies in the "last mile" of our insurance shopping experience, where we orchestrate intricate, multi-step transactions with external systems. This is a high-stakes environment where precision and reliability are paramount, especially given the industry's lack of modern APIs. You will be responsible for building custom orchestration layers that navigate internal and external interfaces with exceptional accuracy, managing asynchronous states and ensuring real-time system reliability.
- • Your initial focus, Phase 1, will involve deep immersion in the code. You will gain a comprehensive understanding of both the technical intricacies and the complex business logic of our core product, recognizing that each insurance provider operates with unique logic and behaviors. Following this learning phase, you will lead the incremental refactoring of our existing automation systems. This includes designing and implementing new architectural standards and collaborating closely with engineers to ensure the development of a predictable and highly testable new system.
- • As the architecture matures and stabilizes, you will transition into Phase 2. In this phase, you will spearhead the development of the next generation of internal tools, employing an AI-first approach. The goal is to build systems that can seamlessly support our growth from 5 million to an ambitious 50 million users, ensuring scalability and efficiency.
- • This role offers unparalleled ownership. With direct access to the co-founder/CTO, you will experience a work environment free from red tape and slow-moving processes. Your innovative ideas can be pitched, built, and deployed within days, allowing you to see the immediate impact of your work.
- • You will be part of a stellar, high-talent team. We maintain a rigorous bar for talent, fostering a small but mighty group of passionate, like-minded peers who are dedicated to accomplishing significant goals. This collaborative environment encourages speed and efficiency in problem-solving.
- • This is a hands-on position, with approximately 80% of your time dedicated to technical work. You will be actively involved in transitioning our legacy automation systems into a more decoupled and scalable architecture, getting your hands dirty to solve difficult problems alongside your team.
- • You will leverage the vast volume of customer data available to us. As a consumer-facing business with over 5 million customers, we possess extensive data on user behaviors, including driving/telematics, shopping, and payment patterns. This data is crucial for guiding our product, technical, and business decisions, providing a rich foundation for innovation.
- • The technical challenge involves evolving our current automation systems, which were initially built for speed rather than scale. These systems currently represent a web of tightly coupled business logic and database access, making changes risky and failures difficult to debug. Your mission is to transform this into a resilient and scalable framework.
- • You will be responsible for ensuring our systems can gracefully handle external interface changes and scale across numerous new categories with minimal manual oversight. This requires a deep understanding of asynchronous job processing, state management, and robust error handling.
- • The ideal candidate is a "Player Coach" – someone who likely founded a company or served as a lead architect in an early-stage startup. You are a builder at heart, comfortable working directly with code and collaborating closely with your team in the trenches.
- • You are a "Detective" – obsessed with success rates and driven to hunt for edge cases within complex business logic. You will not rest until the root cause of any script failure is fully understood and resolved.
- • You are a "Systems Thinker" – possessing a high bar for system design, particularly for offline, asynchronous jobs. You understand the unique demands of asynchronous work, requiring stricter standards for decoupling, state management, and sophisticated failure retry logic compared to synchronous online systems.
- • Our tech stack includes TypeScript (Nest.js, React), GraphQL, and AWS (ECS/EKS, Lambda), providing a modern and robust platform for development.
🎯 Requirements
- • Proven experience as an Engineering Manager or Tech Lead in a fast-paced, startup environment, with a strong track record of building and scaling complex systems.
- • Deep technical expertise in backend development, system design, and architecture, particularly with asynchronous and offline job processing.
- • Hands-on coding ability and a willingness to spend a significant portion of your time (approx. 80%) writing code and directly contributing to technical solutions.
- • Experience with our tech stack: TypeScript (Nest.js, React), GraphQL, AWS (ECS/EKS, Lambda), or similar modern technologies.
🏖️ Benefits
- • Competitive salary and equity opportunities, reflecting your experience and contribution.
- • Comprehensive health, dental, and vision coverage.
- • Generous paid time off and paid parental leave.
- • 401(K) plan with employer matching.
- • Wellness benefits and other perks designed to support employee well-being.
Skills & Technologies
JavaScript
TypeScript
React
AWS
GraphQL
Onsite
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.
