Top Tech Jobs & Startup Jobs in Chicago, IL

Develop and execute go-to-market strategies for healthcare and employee benefits products. Responsibilities include market and competitive analysis, product positioning and messaging, marketing collateral, product launches, sales enablement, cross-functional collaboration, client feedback analysis, and performance measurement. The role translates complex product capabilities into compelling customer-focused stories and supports thought leadership initiatives.

Own and scale automated testing frameworks, expand end-to-end coverage, lead QA initiatives, and perform automation, API, mobile, and regression testing. Collaborate cross-functionally to define coverage, analyze risks, debug defects, and improve CI/CD test execution through GitHub Actions. Champion quality engineering practices across the organization while supporting web and mobile application stability.

Administers compensation, commission, bonus, and incentive programs; calculates and audits payouts; partners with Payroll, Finance, HRIS, and business leaders; builds Power BI dashboards and automated workforce reports; analyzes compensation and people data; ensures data integrity; and improves Total Rewards processes through automation and documentation.

Provides legal counsel on employer-sponsored health and welfare benefit plans, including ERISA, HIPAA, ACA, COBRA, fiduciary governance, claims, appeals, and regulatory compliance. Drafts plan documents and participant communications, negotiates client and vendor contracts, supports audits and investigations, monitors legal developments, resolves benefits disputes, and trains stakeholders. Requires a J.D., active U.S. law license, and 5–10 years of relevant legal experience.

Analyzes complex healthcare data to identify trends, develop statistical and machine learning methodologies, and produce actionable insights. Builds dashboards and reports, supports product and business decisions, promotes data literacy, and collaborates with cross-functional teams. The role also ensures analytics practices comply with healthcare privacy, governance, security, and regulatory requirements, including HIPAA.

Lead employer-focused sales strategy for CirrusMD’s virtual care solution. Responsibilities include developing territories, generating new business with employers and benefits consultants, building C-level relationships, negotiating contracts, presenting solutions, achieving revenue targets, providing market feedback, and partnering with sales operations and account management. The role is remote within the United States and requires significant domestic travel.