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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 lead the development and scaling of Jerry's sophisticated AI platform, which already automates over 70% of inbound sales and service requests (50k+ chats monthly). The role sits at the intersection of product, engineering, and applied AI, reporting directly to the COO.
Key responsibilities include:
- End-to-end ownership of the AI platform roadmap and customer-facing agentic AI experiences, from conception through rollout
- Partner with engineering to design prompt strategies, evaluation frameworks, and guardrails that balance latency, cost, and accuracy
- Serve 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
- Address current technical debt: prompts powering chatbots, photo validation, and back-office automation are scattered across six locations with no unified platform or clear ownership
You are a technologist who reads model release notes, builds custom AI workflows, and thinks in systems. You are comfortable with API design, system architecture, SQL, and data analysis. You can translate complex technical concepts for any audience and navigate tradeoffs pragmatically. You have 4+ years in technical roles (forward-deployed engineering, technical product management, or similar) at fast-paced startups, with a track record of turning complex strategic ideas into scalable, production-grade products.
