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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 own the strategy and execution for Jerry's AI platform, reporting directly to the COO. Your scope spans two layers: maintaining the current system while architecting its future state.
In the first few months, you'll learn the prompt engineering workflow, understand how the tech stack (Propelix, Botly, CRM, GitHub, Replit) interacts, and identify bottlenecks. You'll then transition to owning 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, and operations 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, determining when they're ready for serious investment. 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 conversations, translating complex concepts for any audience. You're an experimenter constantly tinkering with new capabilities, data-driven with SQL familiarity, and pragmatic about technical tradeoffs.
Ideal candidates have 4+ years in technical roles (forward deployed engineering, technical product management, or similar) at fast-paced startups, with passion for AI systems including modern LLMs, and a track record of turning complex strategic ideas into scalable, production-grade products.
