Roles › Senior Payroll Specialist
Chicago, IL
Senior Payroll Specialist jobs in Chicago, IL
3 open roles from 3 employers. Checked Oct 6, 2026.
What these openings look like
3 employers are hiring here: Jones Lang LaSalle, Cboe Global Markets and PEAK6. 2 of the 3 publish a pay range, running $79,000 to $108,900 a year. The rest do not say. Every posting is full time. The most recent went up on Sep 29, 2026.
Every listing links to the employer's own application. Nothing is posted here on their behalf, and nothing is reposted from anywhere else.
Open roles
What it pays here
Only some employers publish a range. These are the ones that did, as written in their own postings:
- $84,150–$108,900 a year
- $79,000–$98,750 a year
What they ask senior payroll specialist candidates here
Drawn from the 3 open postings on this page. The ones that come up across several employers are near the top.
An employee lives in one state and works in another. How do you make sure withholding is right?
What they are checking: Real command of multi-state tax rules, which is where most payroll errors in a national firm happen.
Payroll is due tomorrow and you find a large unexplained variance in the register. What do you do?
What they are checking: Whether they follow a calm reconciliation process under deadline instead of pushing through or panicking.
Walk me through how you reconcile payroll to the general ledger each cycle.
What they are checking: Whether they own accuracy past the pay run and understand payroll's link to accounting.
How do you keep up with changes in local payroll taxes and leave laws across many jurisdictions?
What they are checking: Whether they have a reliable habit for staying compliant as rules change across states and cities.
Tell me about a payroll process you improved. What was slow or error-prone, and what changed?
What they are checking: Whether they can drive the process optimization the posting asks for and measure the result.
An upset employee says their paycheck is short and they need the money now. How do you handle it?
What they are checking: Whether they combine empathy with a clear process, including off-cycle options and accurate follow-up.
How do you handle supplemental wages like bonuses and commissions, and what withholding methods do you use?
What they are checking: Knowledge of rules that matter in a firm with many brokers paid through commissions and bonuses.
Tell me about a mistake that made it into a payroll. How did you fix it and keep it from happening again?
What they are checking: Whether they own errors and add controls rather than only correcting the single case.
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