SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
Jerry.ai is a pre-IPO, profitable insurtech startup ($240M raised, 5M+ customers) building an AI-powered platform to manage car ownership and home services. The company pioneered generative AI in insurance before off-the-shelf platforms existed, building proprietary infrastructure that now handles a significant share of customer interactions end-to-end.
You will lead the technical product strategy for Jerry's AI engineering and systems platform, reporting directly to the COO. Your scope covers two layers: maintaining the current AI platform's reliability while architecting its future state.
In your first months, you'll learn the prompt engineering workflow by writing and updating prompts, understanding how various tech stacks (Propelix, Botly, CRM, GitHub, Replit) interact, and identifying bottlenecks. You'll then own the platform strategy, including: (1) Prompt consolidation—defining and executing a migration strategy to move prompts from six separate locations onto a unified platform, aligning engineering, data, operations, and other teams; (2) Chatbot prioritization—owning the technical prioritization queue and keeping teams coordinated without adding process overhead; (3) Emerging technology decisions—tracking voicebot and computer use capabilities, determining investment thresholds, owning the OpenAI relationship, and managing Jerry's presence in the ChatGPT store.
You are a technologist deeply familiar with AI systems, LLMs, and modern AI workflows. You're a systems thinker comfortable with API design and system architecture discussions, able to translate complex concepts for any audience. You're an experimenter constantly tinkering with new AI capabilities and a pragmatist who can navigate technical tradeoffs. You're data-driven with SQL familiarity and comfortable diving into data to validate hypotheses.
Ideal candidates have 4+ years in technical roles (forward deployed engineering, technical product management, or similar) at fast-paced startups, with a passion for AI systems and a track record of turning complex strategic ideas into scalable, production-grade products.
