Payroll Lead
About The Position
The Lead Payroll Specialist serves as the functional expert and operational lead for payroll, overseeing end-to-end multi-state payroll processing, compliance, and continuous improvement. The role is the primary payroll subject matter expert, ensuring accuracy, resolving complex issues, improving processes, and partnering across HR, Finance, and leadership. This contract-to-hire role is based in Chicago, Illinois, and follows a hybrid schedule with on-site work on Monday and Tuesday. The work environment is a dynamic financial services organization spanning fintech, insurance, and investment sectors, comprising nine companies. The team is collaborative, and the role offers opportunities for growth and exposure to senior leadership.
Requirements
- 10–15 years of payroll experience, including lead experience.
- Deep expertise in multi-state payroll processing and a strong command of federal and state compliance, tax regulations, and wage and hour laws.
- Strong analytical skills and proficiency in Microsoft Excel, including the ability to build and interpret payroll reports.
- Excellent communication skills, including the ability to explain complex payroll topics to non-payroll stakeholders.
- Highly organized and detail-oriented, with the ability to manage competing priorities under tight deadlines.
- Technology-forward mindset and willingness to seek ways to automate, improve, and scale payroll processes.
Nice To Haves
- Hands-on Workday Payroll experience is strongly preferred.
- Certified Payroll Professional (CPP) designation preferred.
- Experience with NetSuite or similar general ledger systems is a plus.
Responsibilities
- Own and execute biweekly multi-state payroll processing for exempt and nonexempt employees across multiple legal entities using Workday Payroll.
- Collect, audit, calculate, and enter payroll information accurately to maintain payroll data integrity.
- Serve as the primary escalation point for complex payroll questions and year-end payroll processing, including W-2 preparation, balancing, adjustments, and amendments.
- Ensure compliance with federal, state, and local payroll regulations, including FLSA, wage and hour laws, overtime requirements, and termination pay regulations.
- Manage payroll tax obligations, including registering in new states, closing inactive accounts, and resolving tax notices with third-party providers.
- Partner with internal teams to support onboarding, offboarding, compensation changes, deductions, and benefits administration.
- Develop and maintain payroll reporting and analytics to support business and leadership needs.
- Reconcile monthly payroll bank transactions and support month-end close activities, including journal entries and general ledger reconciliations.
- Identify opportunities to automate manual payroll processes and improve operational efficiency.
Benefits
- Medical insurance
- Dental insurance
- Vision insurance
- Critical illness, accident, and hospital coverage
- 401(k) retirement plan with pre-tax and Roth post-tax contributions available
- Voluntary life and AD&D insurance for employees and dependents
- Short- and long-term disability
- Health Spending Account (HSA)
- Transportation benefits
- Employee Assistance Program
- Time off or leave, including PTO, vacation, or sick leave
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What This Job Offers
Career Level
Senior
Education Level
No Education Listed
