• Lead the entire engineering organization (approximately 25 people) across all product engineering teams. • Define what an AI-first engineering org actually looks like at Mainstay. • Build an engineering culture where the bar is high, feedback is direct. • Make clear, timely decisions about team composition and performance. • Bring engineering a credible, trusted voice in product decisions. • Partner with the CPO and product managers on org design, hiring, and how engineering should evolve.

• Directly manage up to 20 direct reports, as a single execution unit • Partner with multiple Product Managers to plan roadmaps and sprints • Be accountable for high quality execution on critical and high visibility business objectives • Be responsible for making tradeoffs between feature work and addressing long term technical debt • Be responsible for excellence in software quality, engineering practices and operations • Lead the team through standard Agile processes, such as backlog management, stand ups, retros, etc. • Review and approve engineering designs and be able to set technical direction (in collaboration with a Technical Lead) • Drive cross-org initiatives alongside managing execution responsibilities • Drive career conversations and career plans for your direct reports

The technical challenge: More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc) is complicated, fragmented, expensive and time-consuming. At Jerry.ai, we are building the first mobile app to manage it all. Our insurance marketplace is our core product today, and our ability to automate the end-to-end shopping experience is our core differentiator. The Core Backend Team owns the most critical part of that, the "last mile", where we orchestrate complex, multi-step transactions with external systems to finalize insurance policy purchases. Because the industry lacks modern APIs, we build custom orchestration layers that navigate internal and external interfaces with precision. It is a high-stakes puzzle of asynchronous state management and real-time system reliability. Your challenge will be to evolve our current automation systems to a robust, fault-tolerant framework that can handle external interface changes gracefully and scale across dozens of new categories with minimal manual intervention. Why you will (or won’t) like working here: - Ownership: You’ll report directly to our co-founder/CTO, who is actively involved in product implementation. There is no red tape, no slow-moving processes, and no layers of approvals needed. If you have an idea, you can pitch it, build it, and see it live in days. - Stellar team: We have a very high bar for talent, as a result, we have a small but mighty team that can move fast and accomplish a lot. You will work with likeminded peers who are equally passionate and who care intensely about what they do. - Hands-on: Many of our TLMs are ex-founders, they like getting their hands dirty and solving difficult problems. You will spend 80% of your time doing hands-on technical work (e.g. transitioning our legacy automation systems into a more decoupled, scalable architecture). - Volume of customer data: We are a consumer-facing business (5M+ customers) and have access to a massive amount of customer data across behaviours like driving/telematics, shopping, payment, etc. which helps guide our product, technical and business decisions. What you’ll own: Our first automation system was built for speed, not scale. Today, it’s a web of tightly coupled business logic and database access that makes changes risky and failures hard to debug. - Phase 1: You’ll be deep in the code, learning both the technical and business sides of our core product (insurance is very complex and every insurance provider uses different logic and behaves differently). Then you will lead incremental refactoring of our existing automation systems: designing and implementing new standards and pairing with engineers to ensure the new system is predictable and testable. - Phase 2: As the architecture stabilizes, you’ll shift towards using an AI-first approach to building the next generation of internal tools that will allow us to grow from 5M to 50M users. Who you are: - A Player Coach: You likely founded a company or were a lead architect at an early stage startup. You are a builder at heart and like being in the trenches alongside your team. - A Detective: You are obsessed with success rates. You love hunting for edge cases in complex business logic and won't stop until you understand exactly why a script failed. - A Systems Thinker: You have a high bar for system design, especially for offline, asynchronous jobs. You understand that async work requires much stricter standards for decoupling, state management, and failure retry logic than synchronous online systems. Our tech Stack: TypeScript (Nest.js, React), GraphQL, AWS (ECS/EKS, Lambda). While we appreciate your interest and application, only applicants under consideration will be contacted. Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants. We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits. About Jerry.ai: Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.

The technical challenge: More than 80% of Americans own a car and see it as a fundamental necessity, yet the experience of owning one is stuck in the 90s. Every part of the user journey (shopping for a car, insurance, repairs, etc) is complicated, fragmented, expensive and time-consuming. At Jerry.ai, we are building the first mobile app to manage it all. Our insurance marketplace is our core product today, and our ability to automate the end-to-end shopping experience is our core differentiator. The Core Backend Team owns the most critical part of that, the "last mile", where we orchestrate complex, multi-step transactions with external systems to finalize insurance policy purchases. Because the industry lacks modern APIs, we build custom orchestration layers that navigate internal and external interfaces with precision. It is a high-stakes puzzle of asynchronous state management and real-time system reliability. Your challenge will be to evolve our current automation systems to a robust, fault-tolerant framework that can handle external interface changes gracefully and scale across dozens of new categories with minimal manual intervention. Why you will (or won’t) like working here: - Ownership: You’ll report directly to our co-founder/CTO, who is actively involved in product implementation. There is no red tape, no slow-moving processes, and no layers of approvals needed. If you have an idea, you can pitch it, build it, and see it live in days. - Stellar team: We have a very high bar for talent, as a result, we have a small but mighty team that can move fast and accomplish a lot. You will work with likeminded peers who are equally passionate and who care intensely about what they do. - Hands-on: Many of our TLMs are ex-founders, they like getting their hands dirty and solving difficult problems. You will spend 80% of your time doing hands-on technical work (e.g. transitioning our legacy automation systems into a more decoupled, scalable architecture). - Volume of customer data: We are a consumer-facing business (5M+ customers) and have access to a massive amount of customer data across behaviours like driving/telematics, shopping, payment, etc. which helps guide our product, technical and business decisions. What you’ll own: Our first automation system was built for speed, not scale. Today, it’s a web of tightly coupled business logic and database access that makes changes risky and failures hard to debug. - Phase 1: You’ll be deep in the code, learning both the technical and business sides of our core product (insurance is very complex and every insurance provider uses different logic and behaves differently). Then you will lead incremental refactoring of our existing automation systems: designing and implementing new standards and pairing with engineers to ensure the new system is predictable and testable. - Phase 2: As the architecture stabilizes, you’ll shift towards using an AI-first approach to building the next generation of internal tools that will allow us to grow from 5M to 50M users. Who you are: - A Player Coach: You likely founded a company or were a lead architect at an early stage startup. You are a builder at heart and like being in the trenches alongside your team. - A Detective: You are obsessed with success rates. You love hunting for edge cases in complex business logic and won't stop until you understand exactly why a script failed. - A Systems Thinker: You have a high bar for system design, especially for offline, asynchronous jobs. You understand that async work requires much stricter standards for decoupling, state management, and failure retry logic than synchronous online systems. Our tech Stack: TypeScript (Nest.js, React), GraphQL, AWS (ECS/EKS, Lambda). While we appreciate your interest and application, only applicants under consideration will be contacted. Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws. Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at recruiting@jerry.ai The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants. We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits. About Jerry.ai: Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets. Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started. Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing. Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.