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This position has closed. Wintrust removed this listing from their careers page on Oct 6, 2026. The interview prep below is still useful, and there are similar open roles at the bottom of this page.

Executive Assistant

Wintrust · Rosemont, IL · $27.00–$39.50 an hour · Full time

Posted Aug 5, 2026 · We last checked this listing on Oct 4, 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 would coordinate travel including flights, hotels and car services, and assist with expense reports. Tell me about a trip that fell apart and what you did.

What they are checking: Whether they stay calm and resourceful when travel plans fall apart, because an executive stranded mid-trip needs fast, practical fixes from their assistant.

The posting asks you to anticipate the needs of leadership by proactively managing complex calendars. What does anticipating actually look like?

What they are checking: Whether they actually plan ahead for leadership's needs rather than reacting to requests, which is what makes an executive assistant truly valuable.

The posting names a high degree of personal integrity to maintain trust across senior leadership. What kind of information would you be trusted with, and how do you protect it?

What they are checking: Whether they can be trusted with sensitive leadership information and keep it protected, because discretion is the foundation the whole role rests on.

Tell me about working for someone demanding. What did you learn about how to support them?

What they are checking: Whether they adapt to how a demanding person works and learn from it, because supporting senior leaders means fitting their style, not yours.

This supports FIRST Insurance Funding, a premium finance business, at $27.00 to $39.50 an hour asking three to five years. What would you want to know about the executives you would support?

What they are checking: That they treat the fit with the principals as the deciding factor.

What would you do

You would manage the daily schedule and travel for a chief executive, a president and a chief operating officer. When their calendars conflict, how do you decide?

What they are checking: Whether they can fairly balance three senior executives' competing demands, since juggling conflicting calendars without picking favorites is the hardest part of this role.

You would create the agenda deck for monthly executive meetings by collecting updates from other executives. How do you get those updates in on time?

What they are checking: Chasing senior people for inputs, which requires tact and persistence.

You would coordinate visits of outside guests and candidates. What makes a visitor's day go well?

What they are checking: Attention to the guest experience as a reflection on the firm.

You would handle personal arrangements for executives as well as business ones. How do you hold a boundary while still being helpful?

What they are checking: A real and delicate part of this job, stated in the duties.

About the work

You would set up and prep materials for company-wide meetings. How do you make sure nothing is missing before the room fills?

What they are checking: Whether they prepare thoroughly and check details before a meeting starts, since gaps become very visible once the whole company is in the room.

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.

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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 11 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 200+ 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 The Executive Assistant at First Insurance Funding will be responsible for management of calendars, scheduling of meetings, and coordination of travel for executives. Additional responsibilities include assisting in meeting preparation and event coordination. Ideal candidates will be highly organized, detail-oriented, self-motivated, and enthusiastic individuals who embrace this critical support role and thrive in a client intensive environment. What You'll Do • Managing the daily schedule and travel of CEO, President, and COO. • Scheduling and organizing travel itineraries and travel arrangements (airline, hotel, car services). Assisting with expense reports. • Assist in setting up/coordinating meetings. Working with vendors on external venues. Coordinating catering and meals for meetings. • Keeping Track of monthly executive Meetings. Sending Reminders to Team Members. Creating agenda Deck by collecting and consolidating updates from other executives. • Keeping track & Scheduling special events. Putting resources out for meetings. Creating Name Tags for CEO & Team Members. • Tracking meetings, agenda setting, gathering information, deck assimilation, designing announcement slides for all company meetings. • Support projects for the Managing Sales Directors. • Administrative support including filing, copying, and typing correspondence, presentations, spreadsheets, etc. • Ability to run and manage business, including but not limited to: ordering and coordinating personal travel including car services, flight reservations, restaurant reservation, etc. • Generate and share reports. • Coordinate visits of outside guests or candidates. • All other tasks as assigned and requested Qualifications • 3-5 years of relevant experience • Proven experience of recognizing the necessity of adhering to pre-established timetables without compromising on quality • Anticipate the needs of leadership by proactively managing complex calendars • Ability to manage seamless logistics for meetings and presentations including booking venues and prepping materials • Highly proficient in Microsoft Suite • Background in financial or insurance industry a plus • High degree of personal integrity to build and maintain trust across senior leadership, internal teams and external partners 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 $27.00 - $39.50 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.

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