Engineering Manager

📋 Description

• • Are you a seasoned Engineering Manager with a passion for building robust, scalable systems and a knack for leading talented teams? Jerry Technologies, Inc. is seeking a dynamic and hands-on Engineering Manager to join our innovative team in Toronto, Ontario. This is a unique opportunity to take ownership of critical automation systems that power our groundbreaking car ownership super app, impacting millions of users daily.
• • At Jerry.ai, we're revolutionizing the car ownership experience, an area that has lagged behind in technological advancement for decades. While over 80% of Americans rely on their cars, the journey of owning one – from shopping for a vehicle to managing insurance, repairs, and more – remains fragmented, complex, and often frustrating. Our mission is to change this by creating the first comprehensive mobile app that manages every aspect of car ownership.
• • Our core product, the insurance marketplace, is powered by our unique ability to automate the end-to-end shopping experience. The Marketplace Automation Team is at the heart of this, responsible for the crucial 'last mile' of transactions. This involves orchestrating intricate, multi-step processes with external systems to finalize insurance policy purchases. Given the industry's reliance on legacy systems and a scarcity of modern APIs, our team excels at building custom orchestration layers that navigate complex internal and external interfaces with exceptional precision. This is a high-stakes environment demanding mastery of asynchronous state management and unwavering real-time system reliability.
• • As our new Engineering Manager, your primary challenge will be to evolve our existing automation systems into a highly robust, fault-tolerant framework. You will lead the charge in ensuring these systems can gracefully adapt to external interface changes and scale seamlessly across dozens of new product categories with minimal manual intervention. This role requires a blend of strategic architectural vision and a deep commitment to hands-on technical execution.
• • Why Jerry.ai is the place for you:
• • Unparalleled Ownership: You will report directly to our co-founder and CTO, who is deeply involved in product implementation. We operate with minimal red tape, eliminating slow-moving processes and lengthy approval chains. If you have a compelling idea, you have the autonomy to pitch it, build it, and see it deployed live within days, fostering an environment of rapid innovation and tangible impact.
• • A Stellar Team: We maintain an exceptionally high bar for talent, resulting in a small yet incredibly effective team. You'll collaborate with like-minded, passionate peers who are equally dedicated to their craft and driven by a shared commitment to excellence. This is a team that moves fast, achieves significant results, and fosters a culture of mutual respect and intellectual curiosity.
• • Hands-On Leadership: Many of our Technical Leads and Managers are former founders or have extensive startup experience. They thrive on getting their hands dirty and tackling complex problems head-on. You can expect to spend approximately 80% of your time engaged in hands-on technical work, including leading the transition of our legacy automation systems into a more decoupled, scalable, and maintainable architecture.
• • Massive Customer Data: As a consumer-facing business serving over 5 million customers, we have access to an immense volume of valuable data. This includes insights into user behaviors related to driving/telematics, shopping habits, payment patterns, and more. This rich data landscape is instrumental in guiding our product development, technical strategy, and overall business decisions, providing a data-driven foundation for innovation.
• • What you will own:
• • Our initial automation system was designed for speed, but not necessarily for long-term scalability. It currently comprises a tightly coupled web of business logic and database access, making changes risky and debugging failures a complex undertaking. Your role will be pivotal in transforming this landscape.
• • Phase 1: You will immerse yourself in the codebase, gaining a deep understanding of both the technical intricacies and the complex business logic of our core insurance product. You'll then lead the incremental refactoring of our existing automation systems. This involves designing and implementing new architectural standards, establishing best practices for predictability and testability, and actively pairing with engineers to ensure the successful adoption of these new standards.
• • Phase 2: As the architecture matures and stabilizes, your focus will shift towards leveraging an AI-first approach. You will spearhead the development of the next generation of internal tools designed to support our ambitious growth from 5 million to 50 million users, ensuring our systems are future-proof and capable of handling exponential scale.
• • Our Tech Stack includes:
• • TypeScript (Nest.js, React), GraphQL, AWS (ECS/EKS, Lambda).
• • Jerry.ai is committed to fostering a diverse and inclusive workplace. We are an Equal Employment Opportunity employer and prohibit discrimination based on a wide range of protected characteristics. We also provide reasonable accommodations for individuals with disabilities during the application process. Compensation will be determined based on factors such as skills, experience, qualifications, work location, and market conditions, and may include equity grants.