Job Overview
Location
Toronto, Ontario
Job Type
Full-time
Category
Product Marketing Manager
Date Posted
March 24, 2026
Full Job Description
đź“‹ Description
- • As an Engineering Manager for the Core Product Engine at Jerry Technologies Inc., you will lead the evolution of the company’s critical insurance marketplace automation systems, transforming a legacy, tightly coupled codebase into a robust, fault-tolerant, and scalable framework capable of supporting rapid expansion across new product categories with minimal manual intervention.
- • You will report directly to the co-founder and CTO, operating in a high-autonomy environment where ideas can move from concept to production in days, enabling you to drive technical strategy and execution without bureaucratic delays.
- • Your role will be deeply hands-on, with approximately 80% of your time spent writing, reviewing, and refactoring code alongside your team, guiding the transition from a monolithic automation system to a decoupled, event-driven architecture using modern cloud-native patterns.
- • You will lead Phase 1 efforts to deeply understand the complex business logic of insurance underwriting across multiple providers, then refactor existing automation workflows to improve testability, observability, and resilience, establishing new engineering standards for asynchronous state management and error handling.
- • In Phase 2, you will spearhead the adoption of AI-first approaches to build intelligent internal tooling that automates configuration, monitoring, and optimization of automation workflows, enabling Jerry.ai to scale from 5M to 50M+ users.
- • You will mentor and coach a high-performing team of engineers, fostering a culture of ownership, curiosity, and egoless collaboration, where technical excellence and customer impact are equally valued.
- • You will leverage Jerry.ai’s vast dataset of 5M+ customers — including driving telematics, shopping behavior, payment patterns, and claims data — to inform technical decisions, prioritize automation improvements, and validate system reliability in production.
- • You will work with a modern tech stack including TypeScript (Nest.js, React), GraphQL, and AWS services (ECS/EKS, Lambda), ensuring systems are observable, secure, and cost-efficient at scale.
- • You will partner closely with product, data, and operations teams to align technical roadmaps with business goals, ensuring automation systems support new product launches and regulatory compliance across U.S. states.
- • You will champion engineering best practices such as contract testing, chaos engineering, and incremental migration strategies to reduce risk during system evolution while maintaining 99.9%+ uptime for critical customer-facing transactions.
🎯 Requirements
- • Proven experience as a hands-on engineering leader or lead architect in a fast-paced startup environment, with a track record of founding or scaling technical systems from early stages.
- • Deep expertise in designing and refactoring complex, asynchronous, distributed systems — particularly those involving external API integrations, state management, and failure recovery patterns.
- • Strong proficiency in TypeScript and modern backend frameworks (e.g., Nest.js), with practical experience building and operating services on AWS (ECS, EKS, Lambda) at scale.
- • Demonstrated ability to mentor and grow engineering teams while maintaining high technical standards and delivering production code regularly.
- • Excellent systems thinking skills, with a passion for diagnosing edge cases, improving success rates, and building observable, testable, and maintainable automation workflows.
- • Experience working in regulated or complex domains (e.g., insurance, fintech, healthcare) is a strong plus, with ability to quickly grasp intricate business logic and translate it into resilient technical solutions.
🏖️ Benefits
- • Comprehensive health, dental, and vision coverage for employees and dependents.
- • Generous paid time off (PTO) and paid parental leave policies to support work-life balance and family needs.
- • 401(K) plan with employer matching to help build long-term financial security.
- • Wellness benefits including mental health resources, fitness stipends, and ergonomic support for remote or hybrid work.
- • Equity opportunities as part of the total rewards package, allowing employees to share in the company’s long-term success.
- • Access to a mission-driven culture with direct access to leadership, rapid iteration cycles, and the opportunity to impact millions of car owners through innovative AI-powered solutions.
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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