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 highly motivated and experienced Tech Lead Manager, Automation to join our dynamic team in Toronto, Ontario. This is a unique opportunity to take ownership of 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 still trapped 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 every aspect 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 competitive advantage.
• • The Marketplace Automation Team is at the forefront of this innovation, tackling the most challenging part of the process: the "last mile." This involves orchestrating intricate, multi-step transactions with a myriad of external systems to successfully finalize insurance policy purchases. Given the current landscape of the insurance industry, which often lacks modern APIs, we are tasked with building sophisticated custom orchestration layers. These layers must navigate both internal and external interfaces with exceptional precision, presenting a high-stakes puzzle of asynchronous state management and real-time system reliability.
• • Your primary challenge as Tech Lead Manager, Automation will be to evolve our existing automation systems into a highly robust, fault-tolerant framework. This new framework must be capable of gracefully handling external interface changes, a common occurrence in this industry, and scaling seamlessly across dozens of new product categories with minimal manual intervention. You will be instrumental in ensuring our platform remains resilient, efficient, and ready for hyper-growth.
• • This role offers 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, eschewing slow-moving processes and unnecessary 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 tangible impact.
• • You will join a stellar team characterized by a very high bar for talent. This has resulted in a small but incredibly effective 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 an environment where you can learn, grow, and contribute alongside some of the best in the industry.
• • We believe in a hands-on approach. Many of our Tech Lead Managers are former founders or have extensive experience in early-stage startups. They thrive on 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. This will involve transitioning our legacy automation systems into a more decoupled, scalable, and maintainable architecture, directly contributing to the technical foundation of our future success.
• • The volume of customer data at Jerry.ai is immense. As a consumer-facing business serving over 5 million customers, we have access to a vast amount of data spanning driving behavior (telematics), shopping habits, payment patterns, and more. This rich dataset is invaluable, guiding our product development, technical decisions, and overall business strategy, providing a data-driven foundation for all our initiatives.
• • 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. Consequently, it has become a complex web of tightly coupled business logic and database access, making changes risky and failures difficult to diagnose. Your role will be to untangle this complexity.
• • Phase 1 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 complex domain, with each provider employing unique logic and exhibiting distinct 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 actively pairing with other engineers to ensure the new system is predictable, testable, and maintainable.
• • As the architecture stabilizes and matures, Phase 2 will see you shift towards an AI-first approach. You will leverage cutting-edge AI technologies to build the next generation of internal tools. These tools will be crucial for enabling our ambitious growth from 5 million to 50 million users, ensuring our platform can handle the demands of massive scale.
• • 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 fundamentally a builder who enjoys working directly with the team in the trenches. You are a "Detective" at heart, obsessed with success rates, adept at hunting for edge cases within complex business logic, and driven to understand the root cause of every failure. Furthermore, you are a "Systems Thinker" with a high bar for system design, particularly for offline, asynchronous jobs. You understand the critical importance of strict standards for decoupling, state management, and failure retry logic in asynchronous systems, recognizing their unique challenges compared to synchronous online systems.
• • Our current tech stack includes TypeScript (Nest.js, React), GraphQL, and AWS services such as ECS/EKS and Lambda. You will be working with these technologies to build and enhance our platform.