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Jerry is a YC-backed, profitable Series C startup with 5M+ customers building the first AI-powered advisor to manage physical assets (cars, homes, motorcycles, RVs, boats). You'll own the AI systems layer of a consumer product used by millions, working with LLMs, agents, and internal APIs applied to a fragmented $2T market.
The core technical challenge is not in prompts but in the systems around them: what agents are allowed to do, how pieces fit together, where guardrails go, and what 'correct' means when output isn't deterministic. Jerry built proprietary infrastructure before off-the-shelf platforms existed, now handling 70% of inbound sales and service requests—over 50,000 chats monthly in production at scale. This system has outgrown ad hoc ownership and needs strategic leadership.
You'll decide what to build next in AI and make the case for it. Partner with OpenAI to evaluate and deploy next-generation voice models and workflow automation. Evaluate emerging AI technology (voicebot, computer use agents, beyond), prototype what's worth building, and make investment calls. Design evaluation frameworks and guardrails, making real tradeoffs between latency, cost, and accuracy in a regulated production environment. Set the technical bar for chatbot systems, shape what the prompt engineering team builds, and keep architecture sound as it scales. Build new automations across record disputes, email/callout reduction, document validation (licenses, proof of insurance). Work directly with subject matter experts to turn domain knowledge into systems that behave correctly.
You'll have a flat org, ambitious goals, and direct access to founders and execs. The company is fully remote with offices in Palo Alto, New York, Chicago, and Toronto.
