Job Details

Executive Personal Assistant
Chicago, IL
30–40 hours per week, flexible/as needed

We are seeking a highly capable and trustworthy Executive Personal Assistant to support three business partners in both professional and personal matters. The ideal candidate will be based in Chicago and provide flexible support aligned with the client’s schedule, which involves regular travel.

Responsibilities may include but are not limited to:

• Manage and maintain calendars and schedules
• Coordinate appointments and meetings
• Supervise business vendors
• Conduct product and service research
• Arrange domestic and international travel
• Oversee vehicle maintenance and related tasks
• Troubleshoot and resolve basic tech issues

Requirements:

• Prior experience in a personal or executive assistant role
• Strong technical proficiency (e.g., Google Workspace, Microsoft Office, basic troubleshooting)
• Excellent communication and interpersonal skills
• Friendly, positive, and professional demeanor
• Proven ability to work independently, manage time, and prioritize tasks effectively
• Discretion and confidentiality are essential

Additional Requirements:

• Ability to provide at least three professional references
• Successful completion of a State of Illinois criminal background check
• Willingness to sign a confidentiality agreement upon hire