Payroll Team Lead

PEAK6•Chicago, IL

8d•$79,000 - $98,750•Hybrid

About The Position

As Lead Payroll at PEAK6, 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 PEAK6's diverse business lines. If you love solving complex payroll problems and thrive in a fast-paced, technology-forward environment, this role is for you.

Requirements

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

Nice To Haves

Certified Payroll Professional (CPP) designation preferred; FPC considered
Experience with NetSuite or similar general ledger systems a plus

Responsibilities

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
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
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
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