Payroll Team Lead

Peak6 Investments LLC; Chicago (IL); Hybrid; USD 79,000 - 98,750; Full time

Benefits offered by this job

Healthcare benefits

401k match

Parental leave

Tuition reimbursement

Paid Calm app subscription

Job summary

Peak6 Investments LLC, located in Chicago, is seeking a Lead Payroll professional to manage multi-state payroll operations. In this role, you will oversee payroll processing, compliance, and facilitate cross-functional partnerships within the company.

The ideal candidate has 5–8 years of payroll experience, especially in multi-state environments, along with proficiency in Workday Payroll. This position offers competitive pay, remote work options, and various employee benefits, including healthcare and PTO.

Qualifications

• 5–8 years of experience in payroll within a multi-entity environment.
• Hands-on Workday Payroll experience preferred.
• Strong analytical skills, proficient in Excel.

Responsibilities

• Manage multi-state payroll processing and compliance.
• Serve as the primary contact for payroll-related inquiries.
• Drive automation and improve payroll processes.

Skills

Multi-state payroll processing

Federal and state compliance

Workday Payroll

Analytical skills

Microsoft Excel

Tools

NetSuite or similar systems

Job description

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.

ABOUT THIS ROLE

PEAK6 Payroll Team Lead

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:

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.

OUR REWARDS

We offer a robust package of employee perks and benefits, including healthcare benefits (medical, dental and vision, EAP), competitive PTO, 401k match, parental leave, and HSA contribution match. We also provide our employees with a paid subscription to the Calm app and offer generous external learning and tuition reimbursement benefits. As a hybrid workforce, we offer our employees the ability to work remotely up to two days a week.

Base pay offered may vary depending on job-related knowledge, skills, experience, and office location. This position also may be eligible for a discretionary annual bonus in addition to a range of health & wellness benefits, enhancing your overall compensation package.

Base Salary Range

$79,000-$98,750

PEAK6 is proud to be an equal opportunity employer that does not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. Our hiring practices ensure that all qualified applicants receive fair consideration without regard to these characteristics.

PEAK6 is committed to creating an inclusive and accessible workplace for all candidates, including those with disabilities. We are dedicated to ensuring equal employment opportunities and providing reasonable accommodations to qualified individuals with disabilities. If you require reasonable accommodations to participate in the application or interview process, please contact our HR department at [e-mail]. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.