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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, handling over 50k chats per month with >70% automation of inbound sales and service requests.
You will lead the development and scaling of Jerry's AI platform, sitting at the intersection of product, engineering, and applied AI. The company's AI infrastructure—built entirely in-house—currently powers customer-facing chatbots, vehicle photo validation, and back-office automation. However, prompts and systems are fragmented across six locations with no unified platform or clear ownership. Your mandate is to consolidate this, establish best practices, and own the roadmap for next-generation capabilities including voicebots, computer-use agents, and consumer AI applications.
Key responsibilities include: leading end-to-end development from roadmap to rollout; partnering with engineers on prompt strategies, evaluation frameworks, and guardrails; serving as technical translator between engineering and the broader organization; driving systematic improvement in answer quality and automation rates through experimentation; and collaborating with OpenAI partners on next-generation voice models and workflow automation.
You will report directly to the COO, leading one of the company's most important growth levers. Jerry operates with a flat org chart and offers accelerated career growth for ambitious professionals.
Ideal candidates have 4+ 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 turning complex strategic ideas into scalable, production-grade products. You should be comfortable with SQL, system architecture discussions, and rigorous experimentation.
