Top Tech Jobs & Startup Jobs in Chicago, IL

Provides client service and retirement-plan administration for owner-only 401(k) plans. Responsibilities include answering sponsor and advisor questions, managing plan tasks and communications, supporting compliance projects, coordinating plan setup and termination activities, processing distributions and amendments, completing required tax returns, documenting client work, and handling inbound and outbound calls.

Own multi-state payroll, HRIS administration, reporting, compliance, benefits, leave administration, and employee lifecycle processes for a 240+ employee organization. Manage Paycom data, access, configuration, audits, and analytics; partner with Accounting on payroll reconciliations, tax registrations, general-ledger mapping, and benefit allocations. Lead open enrollment, support audits, mentor an HR Operations Specialist, and serve as an internal HRIS and payroll subject matter expert.

Build and manage relationships with retirement plan advisors and sponsors across a defined territory. Drive new retirement plan sales, provide retirement plan design expertise, manage the sales pipeline, partner with internal and channel sales teams, and participate in marketing events. The role emphasizes in-person relationship building, territory expansion, client consultations, and travel of approximately 20–30%.

Serve as the primary contact for payroll clients after go-live, coordinating implementations, collecting documentation, supporting payroll cycles, troubleshooting, and resolving service cases. Lead client training, create self-service materials, promote adoption of payroll and timekeeping capabilities, and coordinate process improvements. The role requires multi-state payroll experience, strong Excel skills, client communication, attention to detail, and the ability to balance service, implementation, and training responsibilities.

Leads the ERISA department, overseeing retirement plan document production, amendments, notices, audits, QDROs, and EPCRS projects. Serves as the primary technical escalation point for complex ERISA matters, monitors regulatory changes, manages team performance and KPIs, coordinates restatements, and supports client and sales escalations. Maintains project documentation while delivering accurate, timely, and client-focused service.

Manage Defined Benefit, Cash Balance, and 401(k) retirement plans; perform contribution calculations, nondiscrimination and coverage testing, compliance reviews, and plan termination coordination. Collaborate with actuaries on valuations, funding, and plan design while providing guidance to internal and external clients. Track project milestones, maintain CRM documentation, monitor regulatory changes, and communicate complex retirement plan requirements effectively.