JobsChicago Trading Company

Payroll Analyst

Chicago Trading Company · Chicago, IL · Finance and Accounting

Posted Sep 11, 2026 · We last checked this listing on Sep 20, 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.

Behavioral

Tell me about a time you caught an error in payroll before it went out the door. How did you catch it and what did you do next.

attention to detail and whether they take ownership of catching mistakes proactively rather than reactively

Describe a payroll process you improved or automated. What was broken about it and how did you know your fix actually worked.

whether they proactively drive process improvement or just execute what's handed to them

Tell me about a time you had to keep something confidential even though people around you were curious or pressuring you for information.

judgment and discretion handling sensitive compensation and personal data

Tell me about a time you had to explain a payroll or tax concept to someone who had no payroll background, like an employee or a manager.

communication skill translating technical detail for a non-expert audience

Technical

Walk me through how you process a semi-monthly payroll from start to finish for a large multi-state population.

whether the candidate actually knows the end-to-end payroll cycle, not just pieces of it

We process payroll across multiple states plus the UK and Netherlands. What are the biggest compliance traps you've run into working with multi-jurisdiction payroll and how did you handle them.

real exposure to multi-state or international payroll complexity versus surface familiarity

What's your experience with quarterly and annual tax filings, and have you ever had to correct a filing after the fact.

depth of hands-on tax filing experience versus just reviewing what someone else prepared

How would you approach reconciling a payroll account to the general ledger, and what do you do when the numbers don't tie out.

understanding of payroll accounting fundamentals and troubleshooting method, not just data entry skill

Which payroll platforms have you actually worked in day to day, and what's something in Excel you'd build to catch payroll errors before submission.

concrete tool fluency and whether Excel skill is real or just listed on a resume

How do you stay current on changing state and local payroll tax requirements, and can you give an example of a change that actually affected how you processed payroll.

whether their compliance knowledge is active and current rather than static

Situational

Say an employee comes to you upset because their paycheck is short and they need rent money today. How do you handle that conversation while still following process.

service orientation balanced with discipline around controls, not just being nice to make the problem go away

If Accounting flags a discrepancy in a payroll journal entry right before month end close, how do you prioritize that against your regular processing deadlines.

time management and prioritization under competing deadlines, which the job explicitly calls out

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The full job description

As published by Chicago Trading Company.

<div class="content-intro"><p>Chicago Trading Company (CTC) is a premier proprietary trading firm specializing in options market making. &nbsp;Our collaborative culture fuels innovation in quantitative research, systematic trading strategies, and cutting-edge trading technology. &nbsp;For over three decades CTC has provided critical liquidity across derivatives exchanges worldwide - making them fairer, more transparent, and more efficient.</p> <p>We strive to be the most innovative firm in the industry today, tomorrow, and long into the future while upholding ethical excellence. We believe that CTC makes a positive impact on the markets, the lives of our employees, and all the communities to which we belong. Started in 1995 by a team of forward-thinking Traders, we are proud to call ourselves an industry leader that keeps making markets and each other better.</p></div><h2><strong>Payroll Analyst</strong></h2> <p>Chicago Trading Company (CTC) helps the world price and manage risk. We pride ourselves on our strong values, our entrepreneurial spirit, and our commitment to doing the right thing. Our culture is highly collaborative across traders, quants, technologists and development teams who work together to solve the toughest problems our markets have to offer. We strive to make a positive impact on our industry, the lives of our employees, and the communities to which we belong.</p> <p>Are you a hands-on payroll professional with keen attention to detail who thrives at critical thinking and problem solving?&nbsp; We are looking for a motivated and analytical individual with strong technical and interpersonal skills to join our Payroll Team! &nbsp;As a Payroll Analyst, you will ensure the accurate and timely processing, reporting, and support for all payroll related functions.&nbsp; Excellent communications skills, both written and oral, are essential for this role.&nbsp; You’ll play a key role in maintaining the policies and procedures to ensure seamless information flow between Human Capital Management, Tax, Payroll, and the rest of the Finance team.</p> <p>&nbsp;</p> <h2><strong>Responsibilities</strong></h2> <ul> <li>Prepare and process semi-monthly US payroll for over 600 employees and expats across multiple states</li> <li>Review UK and Netherlands monthly payroll, including monthly pension submission and tax payments in coordination with local firms</li> <li>Assist with quarterly and annual tax filings for Federal, State and Local agencies</li> <li>Monitor and respond to employee and external inquiries with a strong service-oriented approach</li> <li>Continuously and proactively implement process improvements and controls to ensure data integrity and minimize errors</li> <li>Partner with Accounting and Tax teams for payroll account and G/L reconciliations, audit inquiries and reporting</li> </ul> <p>&nbsp;</p> <h2><strong>Qualifications</strong></h2> <ul> <li>At least three years of payroll experience, including direct payroll processing</li> <li>Solid understanding of payroll accounting, state and local payroll taxes and compliance requirements</li> <li>Top notch communication, analytical, and problem-solving skills</li> <li>Meticulous attention to detail and strong organization, prioritization and time management skills</li> <li>Ability to exercise discretion when dealing with highly confidential information</li> <li>Hands-on proficiency with payroll platforms</li> <li>Advanced Excel skills</li> <li>Certified Payroll Professional (CPP) designation preferred</li> <li>Legal authorization to work in the U.S. is required. We will not sponsor individuals for employment authorization for this job opening.</li> </ul><div class="content-pay-transparency"><div class="pay-input"><div class="description"><p><strong>Compensation</strong></p> <p>The salary range for this role is listed below. This role is also eligible for an annual discretionary bonus. The discretionary bonus will be dependent upon the individual’s skills, experience, qualifications, and firm performance.&nbsp;</p></div><div class="title">Salary Range</div><div class="pay-range"><span>$90,000</span><span class="divider">&mdash;</span><span>$110,000 USD</span></div></div></div><div class="content-conclusion"><p>Most teams at CTC, with the exception of Trading, follow a hybrid workplace model, subject to change based on business need.</p> <p><strong>Our Benefits&nbsp;</strong></p> <p>We strongly believe in the well-being of our employees and their families so we offer outstanding benefits to support you both professionally and personally. These benefits include generous time off, insurance coverage, paid parental leave, free breakfast and lunch (plus healthy snacks, of course), wellness reimbursement, and a variety of other benefits focused on providing the best employee experience.&nbsp;</p> <p><em>(Disclaimer: interns and contractors are not eligible for benefits at CTC)&nbsp;</em></p> <p><strong>Our Commitment to Diversity, Equity and Inclusion</strong></p> <p>At CTC, we aim to cultivate a workplace that celebrates diversity and each person feels included, engaged and empowered. Where each of us feels we belong. We are committed to having a diverse workforce and are proud to be an equal opportunity employer. CTC does not discriminate on the basis of race, religion, color, national origin, sex, gender, gender expression, sexual orientation, age, marital status, veteran status, or disability status. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform crucial job functions, and to receive other benefits and privileges of employment.&nbsp;</p> <p>If you have a disability and believe you need a reasonable accommodation in order to search for a job opening or to apply for a position, please contact us at info@chicagotrading.com. Note that emails sent to this email account for non-disability related issues, such as following up on an application, will not receive a response.</p> <p><strong>Use of Artificial Intelligence (AI)</strong></p> <p>Information submitted by job applicants may be subject to review and analysis by automated systems, including Artificial Intelligence (AI), as part of the recruitment process. Such systems are utilized to enhance the efficiency and effectiveness of our hiring procedures. Applicants are advised that any information provided may be evaluated by AI tools to ensure an equitable and thorough assessment.</p></div>

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