Top Tech Jobs & Startup Jobs in Chicago, IL

Administer FMLA, ADA, disability, personal, military, and state-specific leaves from initial request through return to work. Serve as the primary contact for employees, clients, managers, and benefits vendors; maintain documentation, timelines, records, and compliance. Provide leave-policy guidance, resolve routine claims and HRIS issues, coordinate benefit and payroll impacts, manage leave technology data, and report on leave metrics and trends.

Configure, test, and support global and US payroll systems for new and existing clients. Responsibilities include payroll implementation, system and workflow configuration, employee data loading, parallel payroll testing, payroll code and benefit setup, compliance reviews, client training, documentation, and backup payroll processing. The role collaborates across payroll, HR, benefits, and implementation teams to ensure accurate, compliant, and efficient payroll delivery.

Owns federal, state, and local payroll tax compliance across a multi-client, multi-state payroll operation. Responsibilities include tax account registration, payroll tax research, auditing and reconciliation, agency notice resolution, amended returns, payments, and quarter-end and year-end compliance. The role partners with payroll teams, vendors, clients, and tax agencies while maintaining accurate records and supporting payroll processing.

Analyze employee benefits renewals, carrier proposals, plan designs, contribution strategies, and financial projections for small and mid-sized business clients. Build RFPs, validate quotes, benchmark market data, model claims and pricing, estimate reserves, and present recommendations to client decision-makers. Coordinate renewal handoffs to benefits support teams while maintaining analytical documentation and improving processes through Excel, Salesforce, proprietary tools, and AI-enabled workflows.

Manage the complete payroll process for assigned clients, ensuring accurate and timely payroll administration. Use ADP Workforce Now, Rippling, and Salesforce CRM to support multi-client payroll operations. Maintain strong attention to detail, meet quality and client service standards, manage deadlines, and build trusted relationships with clients and colleagues.

Lead benefits administration and client service for a portfolio of 20–30 employers. Manage renewals, open enrollment, onboarding, carrier/vendor communications, compliance, and enrollment updates. Serve as primary client contact, mentor Benefits Specialists, and collaborate cross-functionally to ensure high-quality benefits delivery and issue resolution.