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Jerry.ai is a pre-IPO insurtech startup that has raised $240M, serves 5M+ customers, and is profitable. The company is building an AI-powered platform to manage car and home ownership—covering insurance, maintenance, repairs, buying, and selling. Jerry launched car insurance in 2019 and became a top-three broker in the US, leveraging homegrown generative AI infrastructure built before off-the-shelf platforms existed.
You will own the end-to-end product strategy and execution for Jerry's AI agents and automation platform. Currently, the system automates over 70% of inbound sales and service requests (50k+ chats monthly), but the underlying prompts, models, and workflows are fragmented across six separate locations with no unified platform or clear ownership. Your mission is to consolidate, standardize, and scale this critical system.
Key responsibilities include:
- Lead end-to-end development of the AI platform and customer-facing experiences, from roadmap through rollout
- Partner with engineering to design prompt strategies, evaluation frameworks, and guardrails that balance latency, cost, and accuracy
- Act as technical translator between engineering and the broader organization, establishing AI best practices and platform standards
- Drive systematic improvement in answer quality, customer satisfaction, and automation rates through rigorous experimentation
- Collaborate with OpenAI partners to evaluate and deploy next-generation voice models and workflow automation capabilities
- Shape how LLM systems, human-in-the-loop feedback, and computer-use agents redefine the insurance and automotive industries
You will report directly to the COO and own one of Jerry's most important growth levers. The role sits at the intersection of product, engineering, and applied AI, requiring both technical depth and strategic vision.
Ideal candidates have 3+ years in technical roles (forward-deployed engineering, technical product management, or similar) at fast-paced startups. You are deeply passionate about AI systems, modern LLMs, and have a track record of turning complex strategic ideas into scalable, production-grade products. You think in systems, are comfortable with SQL and data analysis, and can navigate technical tradeoffs pragmatically.
