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Jerry.ai is a pre-IPO insurtech startup ($240M raised, 5M+ customers, profitable) building an all-in-one platform for car and home ownership. 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 platform, reporting directly to the COO. Your scope covers two layers: maintaining the current AI system while architecting its future state.
In the first few months, you'll learn the prompt engineering workflow by writing and updating prompts, understanding how the tech stack (Propelix, Botly, CRM, GitHub, Replit) interacts, and identifying bottlenecks. You'll then own the platform strategy:
- Prompt Consolidation: Define and execute the strategy for migrating prompts from six separate locations onto a unified platform. Sequence the work, align engineering, data, operations, and other teams, and drive execution.
- Chatbot Prioritization: Own the technical prioritization queue, keeping the team coordinated without adding process overhead.
- Emerging Technology: Track voicebot and computer use capabilities to identify investment thresholds. Own the OpenAI relationship and Jerry's presence in the ChatGPT store, bringing strategic perspective to AI investment decisions.
You are a technologist who lives and breathes AI, reads release notes when new models drop, and has built custom workflows. You're a systems thinker comfortable with API design and architecture discussions, translating complex concepts for any audience. You're an experimenter constantly tinkering with new capabilities, data-driven with SQL proficiency, and pragmatic about technical tradeoffs.
Required: 4+ years in technical roles (forward deployed engineering, technical product management, or similar) at fast-paced startups. Passion for AI systems, modern LLMs, and a track record of turning complex strategic ideas into scalable, production-grade products.
