SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Jerry.ai is a pre-IPO insurtech startup ($240M raised, 5M+ customers, profitable) building the first comprehensive app to manage car and home ownership. The company pioneered generative AI in insurance before off-the-shelf platforms existed, building proprietary infrastructure that now handles >70% of inbound sales and service requests (50k+ chats monthly).
You will lead end-to-end development of Jerry's AI platform and customer-facing agentic experiences, sitting at the intersection of product, engineering, and applied AI. The role owns a sophisticated system spanning customer chatbots, vehicle photo validation, back-office automation, and emerging capabilities like voicebot and computer-use agents. Currently, AI prompts and workflows are fragmented across six locations with no unified platform or clear ownership—you will consolidate and scale this infrastructure.
Key responsibilities include: leading roadmap and rollout for the AI platform; partnering with engineers on prompt strategies, evaluation frameworks, and guardrails; serving as technical translator between engineering and the broader org; driving systematic improvement in answer quality, customer satisfaction, 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 and lead one of the company's most important growth levers. The org is flat with ambitious goals and accelerated career growth opportunities.
Ideal candidates are technologists deeply familiar with modern LLMs and AI systems; systems thinkers comfortable with API design and architecture; experimenters constantly exploring new capabilities; data-driven with SQL proficiency; and pragmatic about technical tradeoffs. 4+ years in technical roles (forward-deployed engineering, technical product management, or similar) at fast-paced startups, with a track record of turning complex strategic ideas into scalable, production-grade products.
