Jobs › PEAK6

Senior Payroll Specialist

PEAK6 · Chicago, IL · $79,000–$98,750 a year · Full time

Posted Jun 9, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a payroll error you caught or fixed. What did you change afterward?

What they are checking: Whether they own mistakes and fix the process so the same error doesn't happen again.

How do you keep payroll data secure and confidential?

What they are checking: Whether they treat salary and personal data with the care it requires.

How do you stay current on federal, state and local payroll tax changes?

What they are checking: Whether they actively track rule changes instead of waiting for a problem to surface.

What would you do

A trader's large bonus needs to run in the next payroll. What do you check before it goes out?

What they are checking: Whether they know supplemental wage withholding rules and verify approvals on large payments.

An employee says their paycheck is wrong and they're upset. How do you handle it?

What they are checking: Whether they respond quickly and calmly, since pay errors hit people personally.

About the work

Walk me through how you process a bi-weekly payroll from inputs to final approval.

What they are checking: Whether they have a disciplined, step-by-step process with checks that catch errors before money moves.

How do you handle payroll for employees who live in one state and work in another?

What they are checking: Whether they understand multi-state withholding and reciprocity, which matters across PEAK6's many businesses.

How do you reconcile payroll to the general ledger and tax filings each quarter?

What they are checking: Whether they can tie payroll data to accounting and quarterly returns accurately.

How do you handle equity compensation or stock events in payroll?

What they are checking: Whether they understand taxable equity events, which are common at investment and fintech firms.

What payroll systems have you used, and how have you improved a process within one?

What they are checking: Whether they go beyond data entry to make payroll more efficient and accurate.

Practice this interview out loud.

Offer builds a real interview for this exact role at PEAK6 from your resume and this job description, asks the questions one at a time, and tells you what landed. The first one is free.

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The full job description

As published by PEAK6.

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 Sr Payroll Specialist PEAK6 is a leading investment firm headquartered in Chicago. More than 20 years ago, we were one of the first firms to develop sophisticated proprietary technology in our trading business. Today, we leverage our technical ingenuity and operational ability across a number of investment areas, spanning early- to mid-stage growth capital, operational control, trading, and sports management, with an eye toward providing value to the customer. Over the years, we have built and operated several leading financial technology firms and today our team includes a proprietary trading firm, a digital wealth clearinghouse, an outsource provider of flood insurance, a value investment arm, an incubation lab, and more. As a member of the payroll team at PEAK6, you'll have a big impact on the firm by adding your payroll and analytical experience to our organization and employees in a rapidly growing environment and team. Additionally, our diverse business streams afford you the unique opportunity to grow across a variety of verticals, engaging you in unique challenges, projects, and technologies. You'll be responsible for: Process bi-weekly multi-state and multiple location payroll for exempt and non-exempt populations via Workday. Maintain payroll information by collecting, calculating, and entering data into the payroll system. Administer all payroll tax-related tasks including registering for new states, closing old accounts, and resolving all tax notices with third-party payroll systems. Support the payroll manager with year-end W-2 preparation including processing, balancing, adjustments, and amendments. Work directly with external auditors to provide requested information for annual audits. Collaborate with internal partners in Human Resources and Finance to facilitate and improve payroll processes. Partner with Treasury to ensure accurate funding requirements for payroll, taxes, benefits, and related items. Develop ad hoc financial and operational reporting as needed. Update and reconcile monthly payroll bank transactions. Participate in financial month-end close, including preparation of accruals, booking of payroll journal entries, and reconciliation of GL accounts. Utilize technology to drive continuous improvement to PEAK6's payroll processes, reports, and controls. Before you join us, you should have: 5+ years of experience in a fast-paced payroll environment exhibiting proficiency in all aspects of day-to-day payroll operations under the financial umbrella. Strong analytical and problem-solving skills with a high level of attention to detail and accuracy. Working knowledge of federal and state payroll policies, including FLSA laws, overtime, and termination regulations. Certified Payroll Professional (CPP) or Fundamental Payroll Certification (FPC) designation is a plus. Working knowledge of Workday and related reporting tools. Familiarity with general accounting principles and accounting systems; NetSuite experience is a plus. Proficiency in Microsoft Office and payroll software programs. A tech-forward approach to managing day-to-day tasks — we love to automate and make things more efficient, and so should you. Ability to handle and prioritize multiple tasks and meet deadlines in a fast-paced environment. 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 hr@peak6.com. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process. #PEAK6

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