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 platform with $240M in funding and 5M+ customers, building the first comprehensive app to manage cars and homes. The company pioneered generative AI in insurance before off-the-shelf platforms existed, building proprietary infrastructure that now handles a meaningful share of customer interactions end-to-end.
You will own the strategy and execution for Jerry's AI platform, which currently powers customer-facing chatbots, vehicle photo validation, back-office automation, and emerging capabilities like voicebot and computer use. The role bridges two critical layers: maintaining the current system 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), identifying bottlenecks and understanding how different systems interact. You'll then transition to owning platform strategy, including: (1) consolidating prompts from six separate locations onto a unified platform, sequencing work and aligning engineering, data, and operations teams; (2) owning the technical prioritization queue for chatbot improvements while keeping the team coordinated without adding process overhead; (3) tracking emerging technologies like voicebot and computer use to determine investment thresholds, and owning the OpenAI relationship and Jerry's presence in the ChatGPT store.
You are a technologist who lives and breathes AI—reading release notes when new models drop and building 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 capabilities, data-driven with SQL familiarity, and pragmatic about technical tradeoffs. You report directly to the COO and lead one of the company's most important growth levers.
Ideal candidates have 3+ 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.
