Top Payroll Specialist Jobs in Chicago, IL

Serve as subject matter expert for U.S. and Canadian payroll tax compliance. Independently research and resolve complex payroll tax issues, manage agency inquiries, oversee tax adjustments and filings (W-2, 941, T4, etc.), conduct audits/reconciliations, coordinate with vendors and stakeholders, support audits, and drive process and control improvements to reduce risk.

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.

Contract Payroll Tax Specialist responsible for processing, paying, and filing high-volume federal, state, and local payroll tax liabilities; reconciling tax accounts in Oracle; responding to agency notices; performing root-cause analysis and corrections; supporting year-end W-2 activities; managing correspondence; and recommending process improvements and automation.

Manage and enable payroll integrations for clients across 400+ payroll providers, troubleshoot data and system issues, validate payroll data and contributions, guide clients through data transmission, draft procedures, ensure regulatory compliance (SEC, DOL, IRS), and drive process improvements across cross-functional teams.

Process, pay, and file high-volume federal, state, and local payroll tax liabilities for US payroll. Prepare and reconcile tax filings and reports, respond to agency notices, investigate discrepancies, maintain Oracle tax accounts, support year-end W-2 activities, and partner with Payroll, Finance, and Treasury. Monitor tax law changes, manage agency access, handle client and employee inquiries, and recommend process improvements.

Process bi-monthly payroll and reconcile timecards; manage multi-state payroll taxes and compliance; support benefits administration and enrollments; respond to employee payroll/benefits inquiries; maintain HRIS and payroll records; assist with audits (401(k), ACA) and reporting; partner with Finance, brokers, and vendors to resolve discrepancies and improve payroll/benefits operations.

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.

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.

Oversee payroll and wage-hour compliance (primarily California), perform audits and analytics, partner with HRIS/Payroll/Legal/IT, lead remediation, support litigation prevention, and maintain payroll governance for a large non-exempt field workforce.

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.