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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 and selling to insurance, maintenance, and repairs.
You will lead the development of Jerry's customer-facing Agentic AI product, which leverages large language models, AI agents, and internal APIs to deliver a seamless customer experience. The platform currently automates over 70% of inbound sales and service requests (50k+ chats monthly) and is expanding into new capabilities like voicebot, computer use, and consumer AI applications.
In this role, you'll sit at the intersection of product, engineering, and applied AI. You will own the end-to-end roadmap for the AI platform, working directly with the COO. Key responsibilities include:
- Lead development from roadmap through rollout of AI-powered customer experiences
- 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
You are a technologist deeply familiar with modern LLMs and AI systems. You think in systems, are comfortable with technical architecture discussions, and can translate complex concepts for any audience. You have 4+ years in technical roles such as forward-deployed engineering or technical product management at fast-paced startups. You're data-driven, pragmatic about technical tradeoffs, and passionate about turning complex strategic ideas into scalable, production-grade products.
