Executive Assistant to CEO & COO | Elite Calendar & Travel

Wintrust Financial Corporation; Rosemont (IL); On-site; USD 37,000 - 54,000; Full time

Benefits offered by this job

Medical Insurance

Dental Insurance

401(k) with company match

Job summary

Wintrust Financial Corporation is seeking an experienced Executive Assistant to manage complex calendars and travel for the CEO, President, and COO. You will coordinate meetings, prepare materials, and handle expenses with a high level of professionalism.

The role requires 3–5 years of administrative experience, strong MS Office skills, and the ability to work independently in a fast-paced environment. On-site role with family-friendly hours and comprehensive benefits.

Qualifications

• 3-5 years of relevant experience in an administrative/support role.
• Ability to manage complex calendars and scheduling for senior leaders.
• Experience coordinating travel, meetings, venues, and catering.

Responsibilities

• Manage daily schedule and travel for executives (CEO, President, COO).
• Schedule travel itineraries and arrangements (air, hotel, car services).
• Assist with expense reports and meeting setup.
• Coordinate meetings, venues, catering, and materials.
• Support special projects and executive communications.
• Generate and share reports and updates.

Skills

Calendar management

Executive support

Microsoft Office

Travel coordination

Meeting coordination

Tools

MS Office

Job description

Wintrust Financial Corporation is seeking an experienced Executive Assistant to manage complex calendars and travel for the CEO, President, and COO. You will coordinate meetings, prepare materials, and handle expenses with a high level of professionalism.

The role requires 3–5 years of administrative experience, strong MS Office skills, and the ability to work independently in a fast-paced environment. On-site role with family-friendly hours and comprehensive benefits.