Payroll Team Lead

WHO WE ARE

We are PEAK6, a leading investment firm, using technology to find a better way of doing things. The company’s first tech-based solution was developed in 1997 to optimize options trading, and over the past two decades, the same formula has been used across a range of industries, asset classes, and business stages to consistently deliver superior results. Today, PEAK6 seeks transformational opportunities to provide capital and strategic support to entrepreneurs and forward-thinking businesses.

PEAK6’s core brands include PEAK6 Capital Management, PEAK6 Strategic Capital, Apex Fintech Solutions, FOCUS, We Insure, Evil Geniuses, Poker Power, Zogo, and Bruce Markets.

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.

You’ll be responsible for:

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.

• 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 Net Suite 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…