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.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
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'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."
