Top Tech Jobs & Startup Jobs in Chicago, IL

Lead design, build, and operation of AI-powered product features across backend, frontend, and AI systems. Make architecture decisions, drive production deployments, improve code quality and reliability, mentor engineers, and own features end-to-end.

Build and productionize AI features across frontend and backend: document review, entity extraction, quote comparison, embeddings and LLM integrations, prototype from customer feedback, and create scalable reusable systems for insurance workflows.

Provide technical leadership and hands-on engineering across AI, data, backend, and frontend systems. Drive architecture, remove technical risks, set engineering standards, mentor senior engineers, and influence cross-team technical direction.

Build and operate ingestion and transformation pipelines to turn messy insurance data into clean datasets. Design bronze/silver/fact layers, model and tune Postgres and analytical stores, define KPIs and reconciliation checks, orchestrate observable data jobs, and ensure end-to-end data quality for analytics and AI products.

Lead company-level technical direction for an AI-native insurance platform. Own architecture across AI, data, infrastructure, and product; resolve high-impact technical decisions; establish org-wide engineering standards; and mentor senior engineers while partnering with founders to shape long-term technical vision.

Own the full enterprise sales cycle for an AI-powered commercial insurance platform: create demand for a new category, develop business cases, negotiate and close complex deals ($25K–$500K+ ACV), engage executive buyers, expand accounts, and feed market intelligence into product and GTM strategy.

Build AI-powered product features across backend, data pipelines, and UI. Implement RAG, embeddings, vector search, prompt design, and tooling to convert messy insurance documents into reliable, source-cited capabilities and collaborate with product and customer teams.