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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 core differentiator: automating the end-to-end insurance shopping experience and orchestrating complex transactions with 100+ insurance carriers. Today, 60% of policies are sold automatically without human intervention, and 78% of customer inquiries are resolved via AI with 83% positive satisfaction.
In this role, you will lead the development of the next-generation AI system as use cases expand beyond car insurance and new models emerge. Key responsibilities include:
- Setting the technical bar for chatbot systems and shaping the prompt engineering team's roadmap while maintaining architectural soundness at scale
- Building new automations for record disputes, email/callout reduction, and document validation (licenses, proof of insurance)
- Evaluating emerging AI technologies (voicebot, computer use agents) and making investment decisions
- Partnering with OpenAI to evaluate and deploy next-generation voice models and workflow automation
You are a hands-on builder with 5+ years of software engineering experience, ideally at early-stage startups where you owned outcomes end-to-end. You have real depth with AI: you've built with new models within days of release and can articulate why one architecture beats another. You understand the unglamorous production realities: evals, regressions, latency, cost, and failure-handling.
Tech stack: TypeScript (Nest.js, React), GraphQL, AWS (ECS/EKS, Lambda), LLM models (OpenAI, Anthropic Claude, Google Gemini).
