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 that has raised $240M and achieved profitability with 5M+ customers. The company pioneered early adoption of generative AI in the insurance space, building proprietary infrastructure to automate sales and service conversations before off-the-shelf platforms existed. Today, their AI systems handle over 70% of inbound sales and service requests (50k+ chats monthly) and are integrated into the ChatGPT app through a partnership with OpenAI.
As Manager of AI Agents and Automation, you will lead the development and scaling of Jerry.ai's sophisticated AI platform that powers customer-facing experiences across car insurance, home services, maintenance, and repairs. Currently, AI prompts and systems are fragmented across six separate locations with no unified platform or single source of truth. You will own consolidating this infrastructure and establishing it as a strategic growth lever.
Your responsibilities include: leading end-to-end development of the AI platform from roadmap through rollout; partnering with engineering to design prompt strategies, evaluation frameworks, and guardrails that balance latency, cost, and accuracy; serving as technical translator between engineering and the broader organization to establish AI best practices and platform standards; driving systematic improvement in answer quality, customer satisfaction, and automation rates through rigorous experimentation; and collaborating with OpenAI partners to evaluate and deploy next-generation voice models and workflow automation capabilities.
You will report directly to the COO and sit at the intersection of product, engineering, and applied AI. The role requires comfort with technical depth (API design, system architecture, SQL) while maintaining pragmatism about tradeoffs. The company operates with a flat org chart and ambitious growth goals, offering accelerated career development for those seeking expanded scope.
Ideal candidates bring 3+ years in technical roles such as forward-deployed engineering or technical product management 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.
