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.

Serve as a client-facing insurance operations specialist who drives adoption and outcomes across agency accounts. Learn client workflows, diagnose adoption barriers, design interventions (retraining, workflow redesign, champion programs), deliver trainings, create enablement materials, triage technical issues, and partner with CSMs on onboarding, reviews, renewals, and expansion.

Lead end-to-end execution of cross-functional engineering programs: create and maintain program plans, run planning cadence, surface and mitigate risks, translate technical status for stakeholders, and improve scalable delivery processes to ensure timely launches.

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 full-cycle recruiting across roles: define search strategy, source and engage candidates, drive hiring processes, partner with hiring managers and leadership, and improve hiring operations to scale the company.

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.

Develop and deploy LLM-based solutions for document intelligence, semantic search, data extraction, and RAG systems. Design prompts and fine-tuned models, build evaluation pipelines, partner with product and engineering to ship production-ready AI features, and rapidly test new research on real customer data.

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.