Tech Lead Manager, Automation

📋 Description

• • Are you a seasoned technical leader with a passion for building robust, scalable systems and a knack for diving deep into code? Jerry Technologies, Inc. is seeking a Tech Lead Manager, Automation to join our dynamic team in Toronto, Ontario. This is a unique opportunity to take ownership of the most critical automation systems that power our core insurance marketplace, a product that is fundamentally changing how Americans manage their car ownership.
• • At Jerry.ai, we recognize that owning a car, a necessity for over 80% of Americans, is an experience stuck in the past. The entire journey – from shopping for a vehicle to managing insurance, repairs, and more – is often fragmented, complex, expensive, and incredibly time-consuming. Our mission is to revolutionize this by building the first comprehensive mobile app designed to manage all aspects of car ownership. Our insurance marketplace is the cornerstone of this vision, and our ability to automate the end-to-end shopping experience is our key differentiator.
• • The Marketplace Automation Team is at the heart of this automation, specifically handling the crucial "last mile" of the customer journey. This involves orchestrating intricate, multi-step transactions with external systems to successfully finalize insurance policy purchases. Given the industry's reliance on outdated infrastructure and the scarcity of modern APIs, we excel at building custom orchestration layers that navigate complex internal and external interfaces with unparalleled precision. This is a high-stakes puzzle that demands expertise in asynchronous state management and a relentless focus on real-time system reliability.
• • Your primary challenge will be to evolve our existing automation systems into a highly robust, fault-tolerant framework. This new framework must be capable of gracefully handling changes in external interfaces and scaling seamlessly across dozens of new product categories with minimal manual intervention. You will be instrumental in ensuring our automation infrastructure is not just functional, but future-proof and adaptable.
• • You will report directly to our co-founder and CTO, who is deeply involved in product implementation. This means you'll experience a work environment free from red tape, slow-moving processes, and excessive layers of approval. 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 impactful contribution.
• • We pride ourselves on maintaining a very high bar for talent. This has resulted in a small but exceptionally capable team that moves with speed and achieves significant results. You will collaborate with like-minded peers who share your passion and demonstrate an intense dedication to their work. This is a place where you can truly thrive alongside other high performers.
• • This role is inherently hands-on. Many of our Tech Lead Managers are former founders or have extensive experience in early-stage startups, meaning they enjoy getting their hands dirty and tackling difficult problems head-on. You can expect to spend approximately 80% of your time engaged in hands-on technical work, such as leading the transition of our legacy automation systems into a more decoupled, scalable, and maintainable architecture.
• • You will gain exposure to a vast volume of customer data. As a consumer-facing business with over 5 million customers, we have access to an immense amount of data related to user behaviors, including driving/telematics, shopping patterns, payment histories, and more. This rich dataset is invaluable in guiding our product development, technical strategies, and overall business decisions.
• • Your primary ownership will be the evolution of our automation systems. Our initial automation system was built for rapid deployment rather than long-term scalability. Currently, it exists as a complex web of tightly coupled business logic and database access, making changes risky and failures challenging to debug.
• • Phase 1 of your role will involve deep immersion in the codebase. You will gain a thorough understanding of both the technical intricacies and the complex business logic of our core product. Insurance is a highly intricate domain, with each provider employing unique logic and exhibiting distinct behaviors. Following this learning phase, you will lead incremental refactoring efforts of our existing automation systems. This includes designing and implementing new architectural standards and collaborating closely with engineers to ensure the new system is predictable, testable, and maintainable.
• • As the architecture stabilizes and matures, you will transition towards leveraging an AI-first approach. Your focus will shift to building the next generation of internal tools designed to support our ambitious growth from 5 million to 50 million users, ensuring our automation capabilities scale effectively with our user base.
• • We are looking for a "Player Coach" – someone who likely founded a company or served as a lead architect at an early-stage startup. You are a natural builder who thrives on being in the trenches, working alongside your team to solve complex challenges.
• • You are a "Detective" at heart, obsessed with success rates. You relish hunting for edge cases within intricate business logic and will not rest until you have a complete understanding of why a process failed. Your analytical rigor is key to ensuring system reliability.
• • You possess a strong "Systems Thinking" capability. You hold a high bar for system design, particularly for offline, asynchronous jobs. You understand that asynchronous work demands significantly stricter standards for decoupling, state management, and failure retry logic compared to synchronous online systems.
• • Our current tech stack includes TypeScript (Nest.js, React), GraphQL, and AWS services such as ECS/EKS and Lambda.