Jobs › Wintrust

Administrative Assistant

Wintrust · Menomonee Falls, WI · $50,000–$65,000 a year · Full time

Posted Sep 14, 2026 · We last checked this listing on Oct 6, 2026

Apply at Wintrust

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

This role supports TRICOM in Menomonee Falls, including clerical and administrative support to the chief executive. Who have you supported, and what did that involve?

What they are checking: Level of support experience against a role that reaches the top of the company

The posting says you'd act as project lead for special projects at the request of the company president. Tell me about a project you ran start to finish.

What they are checking: Whether they can own a project from start to finish, since the president may assign special projects beyond daily administration.

What would you do

You'd document corporate credit card expenses. How do you handle it when a receipt is missing?

What they are checking: Whether they handle company money carefully and follow up on missing receipts, since expense records must hold up to review.

You'd handle confidential information. How do you decide what you can and can't repeat?

What they are checking: Whether they keep confidential information private, since in a small company loose talk spreads quickly and damages trust.

Priorities here change quickly. How do you handle two people who both need you now?

What they are checking: Whether they handle competing demands calmly and fairly, since the posting says priorities change quickly in this office.

About the work

You'd coordinate meetings, conferences and travel for everyone in the company. Walk me through how you book complex travel.

What they are checking: Whether they already know how to book complex travel well, since the role coordinates meetings and trips for the whole company.

The posting says you act as recording secretary and prepare and distribute minutes. What makes good minutes?

What they are checking: Whether they write minutes that help people who missed the meeting, since good minutes capture decisions and next steps clearly.

You'd participate in recruiting for exempt and nonexempt staff and coordinate temporary employees. What have you done there?

What they are checking: The human resources edge of the role, which is a real duty here

The posting names Word, Excel, Outlook and PowerPoint. What's the most complex thing you've built in any of them?

What they are checking: Whether their Office skills go beyond the basics, since the posting names these tools and the work depends on them.

The posting asks for four to five years of administrative or office administration experience. Where do you sit against that?

What they are checking: Whether their experience meets the stated minimum, since the role expects someone ready to work independently from the start.

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.” TRICOM Inc. of Milwaukee is a top provider of staffing administrative and financial services for privately held staffing companies. We are seeking an enthusiastic professional to join our collaborative team as an Administrative Assistant. In this role, you will have opportunities for growth and the ability to make a great impact on the organization. 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 hourly rate • 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 • Promote from within culture What you’ll do: The Administrative Assistant primarily performs administrative work, including frequent high-level clerical work organizing, scheduling, and coordinating, researching, compiling and exchanging (and sometimes analyzing) information for the CEO. Assists supervisors (usually at the department head or committee level) in implementing department heads, managers, other employees and customers, mainly to assist with information exchange, problems and requests. Work is supervised on a limited basis, as necessary. • Participates in administrative staff meetings and attend other meetings and seminars • Participates in recruitment effort for exempt and nonexempt personnel (excluding managerial levels and above); and helps to coordinate the use of temporary employees • Helps to maintain company organization charts and employee directory • Direct Services, such as maintenance, repair, replenishing supplies, mail files • Composes and writes routine correspondence; maintains up-to-date files • Acts as recording secretary at staff and committee meetings; prepares and distributes minutes • Provides administrative support by entering, formatting, and printing information; organizing work; answering the telephone; relaying messages. • Provides clerical, secretarial and administrative support as required to the CEO of the company. • Coordinates meetings, conferences, and travel arrangements for all members of the company • Documenting corporate credit card expenses • Works independently and within team on special nonrecurring and ongoing projects • Acts as a project lead for special projects, at the request of the company president, which may include planning and organizing company functions, planning and organizing multiple presentations, disseminating information, and coordinating direct mailings • Other miscellaneous duties as needed or assigned. Qualifications: • 4-5 administrative, office administration, or secretarial experience • Associate’s degree a plus • Advanced Computer Skills • Proficient in Word, Excel, Outlook, PowerPoint • Outstanding communication and interpersonal skills • Ability to handle data with confidentiality • Ability to prioritize conflicting demands to accommodate rapidly changing priorities • Ability to participate as part of a team by understanding and accepting the various work styles of others and their roles on the team • Ability to respond to common inquires or complaints from management or staff • Ability to work independently with self-motivation • Excellent attention to detail, organizational, and time management skills • Ability to multitask to accommodate rapidly changing priorities • Excellent attendance 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-$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.

Apply at Wintrust

More administrative assistant roles