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Executive Assistant

Job in Rosemont, Cook County, Illinois, USA
Listing for: Wintrust Financial Corporation
Full Time position
Listed on 2026-08-10
Job specializations:
  • Administrative/Clerical
    Office Administrator/ Coordinator, Virtual Assistant/ Remote Admin, Business Administration
Job Description & How to Apply Below
Location: Rosemont

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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