Top Tech Jobs & Startup Jobs in Chicago, IL

Leads enterprise business systems delivery, enhancements, releases, integrations, production support, governance, and continuous improvement. Manages system reliability, operational processes, vendors, risks, budgets, and stakeholder alignment across HR, operations, and IT. Builds and develops teams of developers, analysts, administrators, and configuration specialists while driving measurable improvements in service quality, efficiency, user experience, and risk reduction.

Supports pricing, reserving, and other actuarial functions through data analysis, data validation, reporting, trend analysis, and business insight development. The intern collaborates with credentialed actuaries and cross-functional partners on insurance projects, tools, documentation, and special initiatives while gaining exposure to multiple actuarial disciplines and products.

Leads hands-on design, development, testing, and production delivery of generative and agentic AI solutions. Builds RAG, automation, knowledge retrieval, developer productivity, and IT operations capabilities; integrates AI with enterprise systems, APIs, data, and cloud services. Ensures security, privacy, observability, evaluation, scalability, and operational readiness while mentoring engineers, documenting reusable patterns, and coordinating technical delivery across architecture, infrastructure, security, data, and business teams.

Leads end-to-end solution design and technical delivery across enterprise insurance applications, including policy administration, billing, ECM, and underwriting systems. Guides development teams, validates technical designs, drives integration consistency, partners with business and architecture stakeholders, mitigates technical risk, and improves system reliability, scalability, and technical quality.