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Jerry.ai is a pre-IPO insurtech startup ($240M raised, 5M+ customers, profitable) building the first comprehensive app to manage car and home ownership. The company pioneered generative AI in insurance before off-the-shelf platforms existed, building proprietary infrastructure that now handles >70% of inbound sales and service requests (50k+ chats monthly).
You will lead end-to-end development of Jerry's AI platform and customer-facing agentic experiences, sitting at the intersection of product, engineering, and applied AI. The role owns the strategic roadmap for modern LLM systems, human-in-the-loop feedback loops, and computer-use agents—consolidating AI infrastructure currently fragmented across six locations into a unified platform.
Key responsibilities include: designing prompt strategies, evaluation frameworks, and guardrails balancing latency, cost, and accuracy; partnering with engineers on system architecture and API design; serving as technical translator between engineering and broader organization; driving systematic improvement in answer quality and automation rates through experimentation; and collaborating with OpenAI partners on next-generation voice models and workflow automation.
You will report directly to the COO, leading one of the company's most important growth levers. The role requires deep technical fluency in AI systems, comfort with SQL and data analysis, ability to navigate complex technical tradeoffs, and a track record of turning strategic ideas into scalable production systems. Ideal candidates have 4+ years in technical roles (forward-deployed engineering, technical product management) at fast-paced startups with demonstrated passion for LLMs and modern AI capabilities.
