Senior Product Manager, AI Agents And Platform - Remote Eligible

About Jerry.ai

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
• 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."