Top Tech Jobs & Startup Jobs in Chicago, IL

Lead Nava’s employee-facing healthcare technology product area. Responsibilities include shaping the roadmap, setting measurable product goals, conducting customer research, improving usability and satisfaction, partnering with support, marketing, engineering, and design, and driving product adoption and engagement. The role requires guiding products from discovery through delivery, achieving product-market fit, and aligning stakeholders around priorities and outcomes.

Build and harden Nava’s shared AI platform for LLM-based products. Responsibilities include reusable context and agent-state management, safe long-running agent execution, sandbox integration, model routing, subagent orchestration, token-cost optimization, tracing, evaluation, testing, and documentation. The role partners with product teams to create maintainable infrastructure that supports production AI features at scale.

Own production data ingestion pipelines for healthcare and benefits data, including normalization, mapping, validation, reconciliation, observability, and secure handling of sensitive information. Unify census data processes, scale the platform, improve identity matching, and build automation and TypeScript tooling. The role requires strong Python and SQL skills, production orchestration experience, reliable testing and data-quality practices, and effective communication with technical and nontechnical stakeholders.

Manage a portfolio of California large-group employer clients (100–2,000 lives), lead renewals, open enrollment, compliance, vendor deployment, and member education. Design benefit strategies, create presentations and financial reporting, strengthen client relationships, and collaborate with internal teams to improve service delivery.