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This position has closed. Wintrust removed this listing from their careers page on Sep 25, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Compliance Officer - Risk Based Testing

Wintrust · Rosemont, IL · $85,000–$110,000 a year · Full time

Posted Sep 21, 2026 · We last checked this listing on Sep 22, 2026

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 training bank staff on a regulation.

What they are checking: The posting names training new compliance staff and assisting with bank staff training.

This is onsite at Rosemont. How does that fit your life?

What they are checking: The posting is marked onsite and states the location.

What would you do

A business line pushes back on your finding. How do you handle it?

What they are checking: Second line testing has no authority, so the finding has to stand on its own.

How do you keep several reviews moving without any of them going stale?

What they are checking: The posting names superior time management measured by deadlines and quality of progress.

About the work

Walk me through a compliance review from scoping to the report.

What they are checking: The posting names conducting and overseeing compliance reviews as the core duty.

How do you build a test that would actually catch the failure you are looking for?

What they are checking: Weak test design is how testing programs miss everything and still pass.

How do you write a workpaper that supports your conclusion on its own?

What they are checking: The posting names preparing documents that provide adequate support for work performed and conclusions reached.

Which consumer banking regulations do you know best?

What they are checking: The posting requires expertise in the laws and regulations governing the bank's activities.

How do you evaluate whether a response to an audit issue is good enough?

What they are checking: The posting names obtaining and evaluating responses to ensure appropriate corrective action.

How do you decide what belongs in a report and what stays in the workpapers?

What they are checking: The posting names drafting audit documents in a pertinent, concise and accurate manner.

Practice this interview out loud.

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

Practice this out loud

The full job description

As published by Wintrust.

Wintrust provides community and commercial banking, specialty finance and wealth management services through its 16 bank charters and nine non-bank businesses. Wintrust delivers the sophisticated solutions of a large bank while staying true to the relationship-focused, personalized service of our community banking roots. We serve clients in all 50 states with more than 200 branch banking locations in Illinois, southwestern Florida, northwestern Indiana, west Michigan and southern Wisconsin and commercial banking offices in Chicago, Denver, Milwaukee, Grand Rapids, Mich., and in key branch banking locations throughout Illinois. Our people are the heart of our business and we are proud to rank consistently as a top place to work. Wintrust is a $66 billion financial institution based in Rosemont, Illinois, and listed on the NASDAQ Global Select Market under the symbol “WTFC.” Why join us? • An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 12 years) and Employee Recommended award by the Globe & Mail (past 6 years). • Competitive pay and discretionary or incentive bonus eligible. • Comprehensive benefit package including medical, dental, vision, life, a 401k plan with a generous company match and tuition reimbursement to name a few • Promote from within culture. Why join this team? • We foster an inclusive environment for an individual to grow and work independently. • Opportunity to interact with management level, experienced professionals - higher visibility. • Wintrust has a great compliance culture that comes from the top. • Gain experience and further your career by joining a growing organization. Position Overview Responsible for overseeing an effective, proactive compliance testing program to assure that the organization maintains the required level of compliance set forth by its regulatory agencies. Provides testing to assure compliance with the various Federal and State laws and regulations governing the conduct of the Bank's affairs while seeking to prevent any penalties, liabilities and any other punitive actions against the Bank, its Directors or employees by ensuring corrective action is implemented promptly. What You’ll Do • Maintain a high level of expertise and knowledge of the requirements of the various laws, regulations and rulings governing the Bank's activities. Keeps abreast of regulatory updates through reading, classes, seminars, etc. • Conduct and oversee compliance reviews. • Assist manager with program oversight and development. • Prepare documents which provide an adequate level of support for the audit work performed, conclusions reached and compliance-related issues. Draft audit documents in a pertinent, concise and accurate manner. • Obtain and evaluate responses to audit issues to ensure appropriate corrective action is taken. • Train new Compliance staff and assist in training Bank staff on compliance regulations as needed. • Responsible for review of workpapers and draft reports to ensure accuracy of audit results. • Exhibit superior time management skills (measured by deadlines and quality of progress and projects completed). Maintain confidentiality of information and protects Bank sensitive information and materials. Qualifications • 3-5 years banking and/or banking compliance. • Bachelor’s degree preferred. • CRCM preferred. Benefits Medical Insurance • Dental • Vision • Life insurance • Accidental death and dismemberment • Short-term and long term Disability Insurance • Parental Leave • Employee Assistance Program (EAP) • Traditional and Roth 401(k) with company match • Flexible Spending Account (FSA) • Employee Stock Purchase Plan at 5% discount • Critical Illness Insurance • Accident Insurance • Transportation and Commuting Benefits • Banking Benefits • Pet Insurance Compensation The estimated salary range for this role is $85,000 - $110,000. Actual salaries may vary based on several factors, such as a candidate’s qualifications, skills and experience. #LI-ONSITE From our first day in business, Wintrust has been proud to serve a variety of unique communities and people from all walks of life. To build a company that reflects the communities we serve, we believe that fostering a unique and inclusive workplace where everyone feels valued and empowered to succeed will support our ongoing success. Wintrust Financial Corporation, including community banking and financial services subsidiaries, is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, age, national origin, disability, veteran status, genetic information, and other legally protected categories.