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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.

Financial Analyst - Investment Accounting

Wintrust · Rosemont, IL · $50,000–$65,000 a year · Full time

Posted Aug 26, 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

Interest rates move and the portfolio's unrealized position moves with them. How do you explain that to someone outside finance?

What they are checking: Translation of a confusing result

What would you do

You find something in a prior period that looks wrong. What do you do?

What they are checking: Escalating an uncomfortable finding

This is based in Rosemont. What would you want to know about the portfolio and the close calendar before you took it?

What they are checking: Whether they diligence the workload

About the work

This role does investment accounting for a bank holding company in Rosemont. What investment accounting have you done?

What they are checking: The specific discipline

How does accounting differ for securities held to maturity, available for sale and trading?

What they are checking: The classification distinction that drives everything here

Walk me through the monthly close for an investment portfolio.

What they are checking: The recurring cycle

How do you value a security that does not trade often?

What they are checking: Fair value judgment where it is hardest

What is an other-than-temporary impairment or credit loss assessment, and how do you approach one?

What they are checking: A consequential judgment in this area

You'd reconcile between the investment system and the general ledger. What causes breaks, and how do you clear them?

What they are checking: Reconciliation as real work

You'd support audit and regulatory reporting. What does an examiner look at in investment accounting?

What they are checking: The regulated setting

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 • Family-friendly work hours Why join this team? • We have a culture that encourages an entrepreneurial spirit • We value teamwork, open communication and collaboration • We offer multiple opportunities for development and upward mobility Job Description Summary The Financial Analyst – Investment Accounting is responsible for processing daily investment activity, reconciling payments, maintaining the investment system data/investment schedules, monthly accounting, pricing and reconciliation activities. The responsibilities include communicating with internal and external parties to ensure timely settlement and proper documentation of trades. What You’ll Do • Provide daily investment trade support for all the company’s bank charters • Prepare general ledger entries and daily reconciliations of cash clearing accounts • Work with the AVP on the month-end close process including pricing of securities • Maintain various investment schedules by manually tracking and documenting activity • Compile documentation and reconcile the investment/debt records to third party reports • Maintain general ledger accuracy and investment system data integrity by following established procedures and controls • Assist with special projects as needed Qualifications • 0-3 years of experience • Bachelor’s degree in accounting preferred • Advanced Excel skills and proficiency in MS Office • Attention to detail and ability to work under pressure with strict time deadlines 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 $50,000 - $65,000 along with eligibility to earn an annual bonus. 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.