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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:
- Own end-to-end development of 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
- Consolidate fragmented AI infrastructure (currently spread across six locations) into a unified platform with clear ownership
You are a technologist who reads model release notes, builds custom workflows, and thinks in systems. You're comfortable with technical conversations about API design and system architecture, can translate complex concepts for any audience, and are data-driven (comfortable with SQL). You have 4+ years in a technical role such as forward-deployed engineering or technical product management at a fast-paced startup, with a track record of turning complex strategic ideas into scalable, production-grade products.
The company operates a flat org chart with ambitious goals and accelerated career growth opportunities. You'll work directly with the COO on one of the company's most important growth levers.
