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Jerry.ai is a profitable, Series C, YC-backed startup with 5M+ customers and $240M in funding, building an AI-powered advisor to manage physical assets. Starting with car insurance in 2019, the company is now expanding into home, motorcycle, RV, and boat insurance, targeting 50M customers by 2030.
The AI & Automation team owns the critical infrastructure that automates the end-to-end insurance shopping experience and orchestrates complex transactions with 100+ insurance carriers. Currently, 60% of policies are sold automatically without human intervention, and 78% of inbound customer inquiries are resolved via AI with 83% positive satisfaction.
As AI Systems Architect, you will lead the design and evolution of the next-generation AI system. Key responsibilities include: setting the technical bar for chatbot systems and guiding the prompt engineering team; building new automations for document validation (licenses, proof of insurance), record disputes, and email/callout reduction; evaluating emerging AI technologies (voicebot, computer use agents) and deciding what to invest in; and partnering with OpenAI to evaluate and deploy next-generation voice models and workflow automation.
You'll own outcomes end-to-end, combining hands-on depth with AI systems and production experience. The role requires real expertise in building with new models, understanding why one architecture beats another, and managing the unglamorous production aspects: evals, regressions, latency, cost, and failure handling.
Tech stack: TypeScript (Nest.js, React), GraphQL, AWS (ECS/EKS, Lambda), and LLM models (OpenAI, Anthropic Claude, Google Gemini).
