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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 the entire car and home ownership experience—from buying/selling to insurance, maintenance, and repairs.
You will lead the development of Jerry's customer-facing Agentic AI product, which already automates over 70% of inbound sales and service requests (50k+ chats per month). The role sits at the intersection of product, engineering, and applied AI, with direct reporting to the COO.
Key responsibilities include:
- End-to-end product development for the AI platform and customer 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
The ideal candidate is a technologist with 4+ years in technical product management, forward-deployed engineering, or similar roles at fast-paced startups. You should be deeply familiar with modern LLMs and agentic AI systems, comfortable with SQL and data analysis, and able to translate complex technical concepts for diverse audiences. You think in systems, experiment constantly, and can navigate technical tradeoffs pragmatically.
Jerry.ai has a flat organizational structure with ambitious goals and strong career growth opportunities. The company is early in leveraging generative AI for insurance and is now consolidating fragmented AI infrastructure across six locations into a unified platform to support new capabilities like voicebots and computer-use agents.
