Top Tech Jobs & Startup Jobs in Chicago, IL

Leads actuarial pricing, risk assessment, reserving, regulatory filings, reinsurance support, forecasting, and performance analytics for stop-loss and large-claim products. Oversees rating manuals, pricing assumptions, reserve estimates, compliance documentation, and management reporting while partnering with underwriting, finance, product, compliance, and reinsurance teams. Serves as a large-claims actuarial subject matter expert, supports product development and risk transfer, and develops staff. Travel may include monthly office visits, industry conferences, and stakeholder meetings.

Provides senior legal counsel across insurance, reinsurance, contracts, privacy, data security, AI governance, health law, regulatory compliance, professional liability claims, and litigation. Negotiates complex agreements, advises on supplemental health products, manages outside counsel and legal budgets, oversees disputes, and supports business initiatives and risk mitigation. Requires a Juris Doctor, active law license, and 10+ years of legal experience.

The Senior Financial Analyst supports monthly and quarterly FP&A, forecasting, reporting, variance analysis, budgeting, capital forecasting, and ad hoc financial analysis. The role partners with business leaders to improve expense transparency, accountability, efficiency, and profitability. It also supports Oracle financial system administration and drives FP&A process improvements through workflow standardization, automation, and appropriate AI adoption.

Provides end-to-end employee technology support across Windows, Microsoft 365, identity, endpoints, devices, and network connectivity. Manages helpdesk tickets, SLAs, onboarding and offboarding, asset records, endpoint configuration, and first-level troubleshooting. Supports Active Directory, Entra ID, Intune, and security escalation activities while documenting solutions and creating knowledge articles. Analyzes recurring issues, improves processes, uses basic PowerShell automation, and assists with broader network, cloud, systems, and cybersecurity initiatives.

Manages supplemental health solution accounts, including customer service, implementations, renewals, enrollment and add-product strategies. Partners with sales teams, brokers, customers, and Blue Plan partners to improve satisfaction, persistency, sales operations, and business processes. Oversees operational escalations, opportunity management, billing and performance tracking, and Salesforce administration and reporting.