Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
Product Marketing Manager
Date Posted
April 7, 2026
Full Job Description
đź“‹ Description
- • As an Engineering Manager for Distributed Systems at Jerry Technologies Inc., you will lead the evolution of the company’s core automation infrastructure, transforming a legacy, tightly coupled system into a robust, fault-tolerant, and scalable framework capable of supporting growth from 5M to 50M users. This role is critical because Jerry.ai’s mission to simplify car ownership hinges on its ability to orchestrate complex, multi-step insurance transactions across fragmented external systems—many of which lack modern APIs—requiring precision, resilience, and deep technical ownership.
- • You will spend approximately 80% of your time in hands-on technical work, diving deep into the codebase to understand the intricacies of Jerry’s insurance orchestration layer, which currently operates as a web of coupled business logic and database access. Your initial focus will be on learning the technical and business nuances of the core product—where insurance provider logic varies significantly—and then leading incremental refactoring efforts to decouple services, improve testability, and establish new engineering standards for reliability and maintainability.
- • You will partner closely with engineers to design and implement new patterns for asynchronous state management, failure handling, and retry logic, ensuring the system can gracefully adapt to external interface changes without cascading failures. This includes evolving the current automation system into a modular, observable architecture that supports rapid iteration and minimal manual intervention as new product categories (e.g., financing, maintenance, safety) are added.
- • As the architecture stabilizes, you will transition toward an AI-first strategy, guiding the team in building next-generation internal tools that leverage machine learning to automate and optimize decision-making in insurance underwriting, pricing, and customer journey personalization—scaling the platform’s intelligence alongside its user base.
- • You will report directly to the co-founder and CTO, operating in a high-autonomy, low-bureaucracy environment where ideas can move from concept to production in days. You’ll join a small, elite team of builder-minded engineers—many of whom are ex-founders—who thrive on solving hard problems and take intense pride in their work, fostering a culture of technical excellence, curiosity, and egoless collaboration.
- • You will gain exposure to one of the largest consumer-facing telematics and behavioral datasets in the auto insurance space, using insights from 5M+ customers’ driving, shopping, and payment behaviors to inform technical and product decisions. This role offers unparalleled opportunity to grow as a technical leader who bridges deep systems thinking with product impact, shaping the foundation of a platform poised to disrupt a $300B+ industry.
- • You will develop expertise in modern cloud-native architectures using AWS (ECS/EKS, Lambda), TypeScript (Nest.js, React), and GraphQL, while advancing your skills in distributed systems design, event-driven orchestration, and AI-integrated tooling—positioning you at the forefront of engineering innovation in consumer fintech and insurtech.
🎯 Requirements
- • Proven experience as a hands-on technical leader or lead architect in early-stage startups or high-growth tech companies, with a track record of founding or architecting complex systems from scratch.
- • Deep expertise in designing and evolving distributed, asynchronous systems with strong emphasis on decoupling, state management, fault tolerance, and retry logic—particularly in environments with unreliable or legacy external APIs.
- • Strong proficiency in TypeScript and backend frameworks (e.g., Nest.js), with practical experience building and scaling services on AWS (ECS/EKS, Lambda) and working with GraphQL APIs.
- • Demonstrated ability to balance hands-on coding with team leadership, including mentoring engineers, driving technical standards, and leading incremental refactoring efforts without disrupting delivery.
- • Exceptional problem-solving skills, with a detective-like mindset for tracing failures in complex business logic and a passion for optimizing system reliability and success rates.
- • Experience working in data-rich environments, leveraging customer behavioral data (e.g., telematics, shopping, payment) to inform technical and product decisions.
🏖️ Benefits
- • Comprehensive health, dental, and vision coverage for employees and dependents.
- • Generous paid time off (PTO), paid parental leave, and wellness benefits to support work-life balance and long-term well-being.
- • 401(K) plan with employer matching to help build long-term financial security.
- • Equity grant opportunities as part of the total compensation package, aligning employee success with company growth.
- • Access to a cutting-edge tech stack (TypeScript, Nest.js, React, GraphQL, AWS) and the chance to work on AI-driven internal tools at scale.
- • Opportunity to work directly with the co-founder/CTO in a fast-moving, innovation-driven culture with minimal bureaucracy and maximum impact.
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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