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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.

BSA Specialist III - Investigator

Wintrust · Rosemont, IL · $28.37–$37.02 an hour · Full time

Posted Sep 10, 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 a case where you recommended closing an account relationship. How did that go?

What they are checking: Willingness to recommend an unwelcome action

What would you do

You need more information and the business line isn't responding. What do you do?

What they are checking: Persistence across internal lines, a named duty

Confidentiality here is a legal requirement, not a preference. What does that mean for how you talk about your work?

What they are checking: Understanding that tipping off is a crime

The posting asks for one to three or more years in this area, prefers a bachelor's degree, and gives an hourly range of $28.37 to $37.02 in Rosemont. Does that fit?

What they are checking: The stated experience and posted pay, confirmed

About the work

This role runs in-depth investigations escalated from alert monitoring. Walk me through how you work an escalated alert from receipt to disposition.

What they are checking: Investigation method rather than alert clearing

The posting requires experience filing Suspicious Activity Reports. Walk me through how you write one so it's useful to law enforcement.

What they are checking: The stated requirement, and whether the narrative is written for a reader

How do you decide whether activity is genuinely suspicious or just unusual for that customer?

What they are checking: The judgment call at the center of the job

What do you understand about the requirements of the Bank Secrecy Act, anti-money laundering rules and the USA Patriot Act that shape how you review an account?

What they are checking: Regulatory grounding, not just process familiarity

How does an Office of Foreign Assets Control review differ from an anti-money laundering review?

What they are checking: Whether the sanctions side is real to them

The posting names automated anti-money laundering software, specifically Actimize. What have you used, and how do you handle a system that generates more alerts than anyone can work?

What they are checking: The named tool plus alert volume judgment

Practice this interview out loud.

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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? • An entrepreneurial culture with opportunity for growth • Play an important role supporting Wintrust’s BSA compliance efforts Position Summary The Specialist III - Investigator position is responsible for in-depth investigations that are escalated from the alerting and monitoring processes and from enterprise-wide referrals. Coverage includes enterprise-wide review of our accountholders and their transactions: looking for unusual or suspicious activity; investigating potential suspects and provide adequate documentation of identified cases; and is responsible for the completion of filing of suspicious activity reports when appropriate. The position supports the overall BSA compliance efforts as required under the Bank Secrecy Act and the Bank's BSA/AML/ USA Patriot Act and OFAC Compliance Program and Procedures. What You’ll Do • Identify and analyze high-risk customers and other identified accounts for unusual and suspicious activity • Provide accurate documentation of the suspicious activity and recommends appropriate actions • Prepare and file Suspicious Activity Reports (SARs) and follow appropriate review, documentation and follow-up steps as outlined in Bank's BSA/AML Program • Maintains confidentiality of reports and documentation as required by law • Review legal requests and conduct account reviews from a BSA/AML/USA Patriot Act perspective • Communicate internally to all lines of business to obtain additional information and further documentation to complete analysis of identified accounts, and provide recommendations for case resolution, including account closure • Provide other assistance as requested to the BSA/AML Officers in the daily responsibilities of managing the Bank's BSA/AML and OFAC Compliance Program Qualifications • One to three years plus in Bank Secrecy, Anti Money Laundering and OFAC • Working knowledge of various laws, regulations and guidance as it relates to BSA, AML and OFAC • Experience filing SARs required. • Must possess critical thinking and problem-solving skills • Experience with automated anti-money laundering software preferred specifically Actimize • Bachelor's degree 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 hourly rate for this role is $28.37-$37.02, along with eligibility to earn an annual bonus. Actual pay rate 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.