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Jerry.ai is a pre-IPO insurtech startup ($240M raised, 5M+ customers, profitable) 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, reporting directly to the COO. Your scope covers two layers: maintaining the current AI platform while architecting its future state.
In your first months, you'll learn the prompt engineering workflow across the company's tech stack (Propelix, Botly, CRM, GitHub, Replit), understanding bottlenecks and system interactions. You'll then own the platform strategy:
- Prompt Consolidation: Define and execute the migration strategy for consolidating 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 for chatbot features. Keep the team coordinated and moving without adding process overhead.
- Emerging Technology Decisions: Track voicebot and computer use capabilities closely to identify when they cross the threshold for serious investment. Own the OpenAI relationship and Jerry's presence in the ChatGPT store. Bring a point of view and influence 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 system architecture conversations, translating complex concepts for any audience. You're an experimenter constantly tinkering with new AI capabilities, data-driven with SQL familiarity, and pragmatic about technical tradeoffs.
Required: 3+ years in a technical role (forward deployed engineering, technical product management, or similar) at a fast-paced startup. Passion for AI systems including modern LLMs. Track record of turning complex strategic ideas into scalable, production-grade products.
Jerry.ai offers comprehensive benefits including health/dental/vision, paid time off, paid parental leave, 401(k) with matching, and wellness programs. Equity grants available.
