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Jerry.ai is a pre-IPO insurtech startup that has raised $240M and achieved profitability with 5M+ customers. The company is building an AI-powered platform to manage the entire car and home ownership experience—from buying/selling to insurance, maintenance, and repairs.
You will own the Agentic AI product strategy and execution, sitting at the intersection of product, engineering, and applied AI. Jerry.ai has been an early adopter of generative AI, building proprietary infrastructure that now handles over 70% of inbound sales and service requests (50k+ chats monthly). However, the underlying prompts and AI systems are currently fragmented across six separate locations with no unified platform or clear ownership.
In this role, you will:
- 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
- Serve as the 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 modern LLM systems, human-in-the-loop feedback, and computer-use agents redefine the insurance and automotive industry
You are a technologist who lives and breathes AI, reads release notes when new models drop, and has built custom workflows. You are a systems thinker comfortable with technical conversations about API design and architecture. You are an experimenter constantly tinkering with new capabilities, data-driven with SQL familiarity, and pragmatic about technical tradeoffs. You have 3+ years in technical roles such as forward-deployed engineering or technical product management at fast-paced startups, with a track record of turning complex strategic ideas into scalable, production-grade products.
You will report directly to the COO, leading one of the company's most important growth levers. Jerry.ai offers a flat org chart, ambitious goals, and accelerated career growth opportunities.
