Founding AI Engineer | Build the Future of Insurance Intelligence. Base pay range: $150,000.00/yr - $200,000.00/yr. This role focuses on building AI-powered systems to interpret complex insurance documents, not just chatbots. The position involves creating reasoning AI that can interpret coverage, identify gaps, and transform how a $1.4T industry operates.
Insurance still runs on 100+ page documents written by lawyers, for lawyers — and professionals spend hours comparing them. We’re developing AI to make these documents readable by humans and machines.
What You’ll Do
Own and evolve a production LLM application stack — designing intelligent, high-performing systems beyond basic RAG
Architect sophisticated LLM workflows for complex policy interpretation
Build multi-step reasoning agents and decision-making systems
Develop evaluation frameworks, monitoring tools, and cost-optimization pipelines
Master vector databases and semantic search for legal and insurance data
About You
Proven experience building and deploying advanced LLM applications
Deep understanding of prompt engineering, agentic systems, and evaluation frameworks
Strong background with LangChain, LlamaIndex, or similar
Thrive in founder-led, fast-moving environments where you take full ownership
Passionate about solving real-world challenges with meaningful impact
This is an opportunity to define the AI foundation of a venture-backed startup working with several of the largest US insurance brokers.
Location: Hybrid if you are based in Chicago. Remote if you are based in either New York or San Francisco.
Must be a US citizen or Green card holder.
Seniority level
Mid-Senior level
Employment type
Full-time
Job function
Industries: Financial Services, Insurance, and Insurance Agencies and Brokerages