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Senior Technical Product Manager, AI Engineering & Systems

Jerry - New York, NY, United States - In-office - posted 2026-08-21

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Jerry.ai is a pre-IPO insurtech startup with $240M in funding, 5M+ customers, and profitability. The company is building an all-in-one platform for car and home ownership management, leveraging generative AI across sales, service, and operations. You will lead the technical product strategy for Jerry's customer-facing Agentic AI platform, which integrates with OpenAI and ChatGPT. Your dual mandate is to maintain the current AI infrastructure while architecting its future state. In your first months, you'll learn the prompt engineering workflow across Jerry's tech stack (Propelix, Botly, CRM, GitHub, Replit) and identify bottlenecks. You'll then own three strategic initiatives: 1. Prompt Consolidation: Define and execute a strategy to migrate prompts from six separate locations onto a unified platform, coordinating engineering, data, and operations teams. 2. Chatbot Prioritization: Own the technical prioritization queue, keeping teams coordinated without adding process overhead. 3. Emerging Technology: Track voicebot and computer use capabilities, determine investment thresholds, and manage the OpenAI relationship and Jerry's ChatGPT store presence. You'll report directly to the COO and lead one of the company's most important growth levers. The role requires deep technical fluency in AI systems, comfort with system architecture and API design, SQL proficiency, and the ability to translate complex concepts for diverse audiences. You should be a pragmatic experimenter who can navigate technical tradeoffs and drive production-grade implementations. Ideal candidates have 4+ years in technical roles (forward deployed engineering, technical product management) at fast-paced startups, with a track record of turning complex strategic ideas into scalable products.

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