Payroll Team Lead

Role: Payroll Lead Contractor

Location: Chicago, IL

Pay: $50 - $55 / hour

Benefits: This role is eligible for medical, dental, vision and 401k.

Job Description:

Payroll Team Lead

As Lead Payroll, you will be the functional expert and operational cornerstone of the payroll team — owning end-to-end multi-state payroll processing, compliance, and continuous improvement. You will be the go-to subject matter expert who sets the standard for quality, drives process excellence, and partners cross-functionally to keep payroll running seamlessly across diverse business lines. If you love solving complex payroll problems and thrive in a fast-paced, technology-forward environment, this role is for you.

You’ll be responsible for:

Payroll Operations

Own and execute bi-weekly multi-state payroll processing for exempt and non-exempt employee populations across multiple legal entities via Workday Payroll

Maintain payroll data integrity by collecting, auditing, calculating, and entering data with a high degree of accuracy

Serve as the primary escalation point for complex payroll questions and discrepancies, resolving issues efficiently and with a strong employee experience in mind

Lead year-end processing including W-2 preparation, balancing, adjustments, and amendments

Compliance & Tax

Ensure compliance with all federal, state, and local payroll regulations including FLSA, wage and hour laws, overtime rules, and termination pay requirements

Manage all payroll tax obligations: registering in new states, closing inactive accounts, and resolving tax notices with third-party systems

Monitor and interpret changes in payroll tax law, proactively communicating impacts and implementing updates

Partner with external auditors to provide documentation and support for annual audits and internal controls

Cross-Functional Partnership

Act as the functional SME for payroll-related inquiries from HR, Finance, and senior leadership — translating complexity into clear guidance

Collaborate to streamline onboarding/offboarding processes, pay changes, deductions, and benefits administration

Work with functional teams to ensure accurate and timely funding for payroll, taxes, and benefits

Contribute expertise during system implementations, upgrades, or integrations — particularly within Workday

Reporting & Process Improvement

Develop and maintain ad hoc payroll reporting and analytics to support leadership decision-making

Reconcile monthly payroll bank transactions and support month-end close, including journal entries and GL reconciliations

Identify and drive automation and efficiency opportunities within payroll operations — we love to eliminate manual work

Maintain payroll policies, procedures, and internal controls documentation to ensure consistency and audit-readiness

Qualifications:

● 5–8 years of progressive payroll experience in a fast-paced, multi-entity environment

● Deep expertise in multi-state payroll processing and a strong command of federal and state compliance, tax regulations, and wage/hour laws

● Hands-on Workday Payroll experience strongly preferred

● Certified Payroll Professional (CPP) designation preferred; FPC considered

● Experience with NetSuite or similar general ledger systems a plus

● Strong analytical skills with proficiency in Microsoft Excel and the ability to build and interpret payroll reports

● A technology-forward mindset — you actively look for ways to automate, improve, and scale payroll processes

● Excellent communicator who can distill complex payroll topics for non-payroll stakeholders

● Highly organized, detail-oriented, and comfortable managing competing priorities under tight deadlines

Addison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. Addison Group complies with applicable state and local laws governing non-discrimination in employment in every location in which the company has facilities. Reasonable accommodation is available for qualified individuals with disabilities, upon request.

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