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Jerry.ai is a pre-IPO insurtech startup that has raised $240M and achieved profitability with 5M+ customers. The company pioneered early adoption of generative AI to automate customer interactions, building proprietary infrastructure that now handles over 70% of inbound sales and service requests (50k+ chats monthly).
You will own the end-to-end development and scaling of Jerry's AI platform and customer-facing agentic experiences. The role sits at the intersection of product, engineering, and applied AI, addressing a critical organizational need: consolidating AI infrastructure currently fragmented across six separate locations into a unified platform with clear ownership of future bets (voicebot, computer use, consumer AI applications).
Key responsibilities include:
- Leading roadmap-to-rollout development for the AI platform and customer experiences
- Partnering with engineering to design prompt strategies, evaluation frameworks, and guardrails that balance latency, cost, and accuracy
- Serving as technical translator between engineering and broader organization, establishing AI best practices and platform standards
- Driving systematic improvement in answer quality, customer satisfaction, and automation rates through rigorous experimentation
- Collaborating with OpenAI partners to evaluate and deploy next-generation voice models and workflow automation
You will report directly to the COO, leading one of the company's most important growth levers in a flat organizational structure.
Ideal candidates bring 3+ years in technical roles (forward-deployed engineering, technical product management, or similar at fast-paced startups), deep passion for AI systems and modern LLMs, and a track record of translating complex strategic ideas into scalable, production-grade products. You should be comfortable with SQL, system architecture discussions, and rigorous experimentation. The role requires someone who is both a technologist and pragmatic systems thinker.
