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This position has closed. Wintrust removed this listing from their careers page on Oct 1, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Associate Account Executive

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

Posted Sep 8, 2026 · We last checked this listing on Sep 30, 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

You'd follow up on outstanding quotes. How do you chase without becoming a nuisance to an agent you will work with for years?

What they are checking: Follow-up as relationship work, not persistence

What would you do

You'd take inbound calls from agents and gather what you need to produce a quote. What do you need to ask, and how do you keep the call short?

What they are checking: The daily call, done efficiently

An agent pushes for a quote that sits outside your authority. What do you do?

What they are checking: Holding a limit against sales pressure

When account executives are out, you'd act as the primary contact for an assigned region. How would you pick up someone else's region cold?

What they are checking: The stated cover duty, which is harder than it sounds

How do you keep several quotes, follow-ups and inbound calls straight on a busy day?

What they are checking: Organization under an interrupt-driven workload

This is with the premium finance business in Northbrook, supporting an inside sales team. What would you want to know about the team and the volume before you took it?

What they are checking: Whether they diligence the actual workload

About the work

This role supports inside sales account executives at a premium finance company in Northbrook. What do you understand about how insurance premium finance works?

What they are checking: Whether they know the product, which is unusual and specific

You'd approve and underwrite quotes up to $750,000. Walk me through what you would look at before approving one.

What they are checking: The named authority limit, tested as real underwriting judgment

You'd help prepare loan agreements. How do you check a document so an error does not get through?

What they are checking: Accuracy discipline on a legal document

The posting asks for at least one year in financial services, bank operations, wires or a similar position. What have you done that is closest?

What they are checking: The stated minimum, checked honestly

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The full job description

As published by Wintrust.

As one of the largest premium finance companies in the country, FIRST Insurance Funding provides full premium finance services, plus additional services built specifically for agencies. We pride ourselves on the variety of incentive programs, services, and technology we offer. This not only helps grow the agents, brokers, and companies we partner with, but also helps them better serve their clients. FIRST Insurance Funding is a subsidiary of Wintrust, a financial services company with more than $66 billion in assets. Why join us? • An award-winning culture! We are rated a Top Workplace by the Chicago Tribune (past 8 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 • With 175+ community bank locations, we offer opportunities to grow and develop in your career • Promote from within culture Why join this team? • We have a culture that encourages an entrepreneurial spirit • We offer multiple opportunities for development and upward mobility What You’ll Do: • Assist all Account Executives in Inside Sales prepare loan agreements. • Approve and underwrite quotes up to $750,000. • Accept Inbound phone calls from agents and obtain necessary information to provide a quote and/or assist with general account management inquiries. • Assist Account Executives with quote follow up. • When Account Executives are out of the office act as the primary Account Executive for an assigned region. Qualifications: • Minimum 1 year experience in financial services, bank operations, wires or similar position • Bachelor degree or equivalent • Strong written and verbal communication skills • Excellent attention to detail • Punctuality and timeliness • Very organized with the ability to multi-task • Must be able to work in a fast-paced environment • Ability to work as part of a team • Basic computer skills including MS Word, MS Excel, Adobe and Internet 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 annual salary range for this role is $50,000 to $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-HYBRID 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.