Top Payroll Specialist Jobs in Chicago, IL

Own global payroll operations and equity administration across employees, EORs, and contractors. Run accurate payroll cycles, perform payroll-to-cash and payroll-to-ERP reconciliations, administer equity programs in Carta, maintain data consistency across HiBob, Carta, Deel, and ERP, and support audits and external advisors with accurate operational data.

As a Payroll Specialist, you'll work with clients in payroll, HR, and PEO environments, using various systems. Responsibilities include ensuring compliance and offering support for payroll processing.

Manage payroll tax filing, remittance, and compliance across US and Canada. Oversee vendor performance (Strada, ADP), research and resolve tax notices, maintain payroll tax setups in Workday and ADP Smart Compliance, support quarter/year-end reconciliations and audits, monitor regulatory changes, improve processes, and provide stakeholder and employee support.

Process payroll tasks including entering timesheets in Paycom, auditing timekeeping, onboarding new hires, maintaining personnel/payroll records, running billing, supporting payroll projects, and performing related administrative duties in a remote role.

Manage end-to-end US payroll processing, administer equity and benefits programs, handle leave and unemployment claims, ensure tax and compliance accuracy, maintain HRIS and cap table records, and partner with Finance, Legal, and HR leadership to support employee payroll and benefits needs.

Lead end-to-end onboarding for PEO clients: build implementation plans for payroll, benefits, tax registrations and HR compliance; manage timelines, parallel payroll reconciliations, platform adoption, cross-functional handoffs, and continuous improvements to implementation tooling and documentation.

Lead and manage payroll processing for North America and Latin America regions, ensuring timely, compliant payroll delivery. Provide technical support, resolve payroll issues, collaborate with HR/Finance/Operations, maintain stakeholder relationships, and produce reports and insights for leadership.

Process multi-state payroll (weekly/biweekly/monthly), maintain payroll records, reconcile accounts, handle garnishments and off-cycle payments, perform year-end W-2 tasks, support Workday/Kronos HRIS (EIB loads), create SOPs/training, resolve employee payroll inquiries, ensure regulatory compliance and internal controls, and manage banking/ACH and wire/check requests.

Remote role connecting candidates to payroll/PEO benefits administration positions. Ideal candidates have 1+ year payroll service bureau or PEO experience working in HRIS, Benefits, or Time modules (with platforms like UKG Ready, isolved, Asure Evolution, ExecuPay, MPAY, ApexHCM, etc.). HireWith provides personalized interview and resume support and access to multiple employer openings nationwide.

The job involves working with payroll services or PEOs, supporting processes related to various payroll systems like UKG and ExecuPay, and aiding in tax notice resolution.

Support daily accounting operations including payroll processing, accounts payable/receivable, purchasing, cash management, general ledger entries and reconciliations, month‑end/year‑end close, financial reporting, audit support, and process improvement to ensure accurate cash flow and financial records.

Manage day-to-day HR operations and own payroll for Philippines-based staff: collect and validate timesheets, calculate pay and statutory contributions, maintain records, ensure Philippine labor law compliance, support onboarding/offboarding and employee relations, and improve HR/payroll workflows.

The HRIS Support Specialist supports HRIS, Benefits, and Time modules for payroll service bureaus or PEO. Responsibilities include providing personalized support, preparing candidates for interviews, and offering access to unadvertised roles.

The role involves connecting candidates with various payroll, HR, and PEO positions while providing personalized support and access to extensive job networks.

Process certified payroll and submit reports via LCPtracker, ensure compliance with Davis-Bacon and prevailing wage laws, review timecards and wage classifications, reconcile payroll discrepancies, monitor fringe benefits and overtime, prepare reports for audits and government agencies, and maintain payroll records.

Lead payroll processing for Latin America, ensuring timely, compliant payroll across multiple countries. Provide technical support, resolve payroll issues, liaise with HR/Finance, maintain local compliance, and report insights to leadership.