The 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. We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store and we have more than 5 million users! About the Opportunity: You will lead the evolution of our AI-powered customer experience and internal AI platform. Your challenge will be to own one of the most strategic areas of the company: how we leverage large language models, agents, and internal APIs to deliver best-in-class, automated customer support and operations. You will sit at the intersection of product, engineering, and applied AI, and require both strategic thinking and hands-on exploration with modern LLM systems. You will build and scale a sophisticated AI system that already includes: - A production-grade conversational AI experience automating >70% of inbound sales and service over chat and SMS - Human-in-the-loop systems for chat evaluation, feedback, and continuous improvement - Internal process automation flows across the company, including automated image review and approval - Jerry.ai insurance and repair quotes available directly in the ChatGPT App, developed in partnership with OpenAI - You will also be responsible for constantly evaluating new models and AI capabilities. This includes evaluating emerging AI technologies, such as voice models and computer use agents, for suitability in a regulated production environment. How You'll Make an Impact: - Lead end-to-end product development for Jerry's AI-powered customer experiences and internal AI platform, from roadmap to rollout. - Partner with engineers and prompt engineers to design and iterate on AI architectures, prompt strategies, evaluation frameworks, and guardrails — making real tradeoffs between latency, cost, accuracy, and user experience. - Be the bridge between engineering and the rest of the org: lead by example for AI best practices and get other teams on board with platform standards. - Own the metrics that matter — answer quality, customer satisfaction, automation rate, escalation quality — and drive systematic improvement through data and experimentation. - Work directly with our partners at OpenAI to evaluate new models and capabilities, and identify the next big leaps in voice, computer use, and workflow automation. Who You Are: - You have 4+ years of experience in technical product management, management consulting, data analytics, or operations at a fast-paced startup. - You're passionate about AI and intrinsically motivated to get hands on with the latest technology. When a new model drops, you read the release notes. You've set up your own AI tools and workflows not because someone told you to, but because you couldn't help yourself. - You're a technologist and a systems thinker. You're comfortable in technical conversations about system architecture, API design, and prompt engineering, and you can translate complex ideas into simple terms for non-technical stakeholders. - You're data-driven, familiar with SQL, and comfortable diving into data to answer your own questions. - You like to own metrics and constantly seek improvement. You're an optimist who asks "how can we" not "if we can." 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.