Executive Personal Assistant

Robert Half
Chicago, IL

On behalf of our client we are looking for an Executive/ Personal Assistant to provide high-level support to a busy executive in Chicago, Illinois. This position requires someone who can manage complex scheduling, coordinate travel, and handle a mix of detail-oriented and personal tasks with discretion and precision. The ideal candidate is highly organized, responsive, and comfortable anticipating needs in a fast-paced environment.


Compensation: $80,000 - $130,000

Monday-Friday

8:30am-5:30pm

Remote primarily will need to be flexible on some light travel local or domestically

Medical, Dental, Vision, PTO, holiday, owner invests money into an account after 1 year


Our specialized recruiting professionals apply their expertise and utilize our proprietary AI to find you great job matches faster


Responsibilities:

• Oversee a dynamic executive calendar, prioritizing meetings, appointments, and shifting commitments to keep daily plans running smoothly.

• Arrange domestic and international travel plans, including itineraries, transportation, lodging, and related logistics.

• Prepare for executive meetings by organizing schedules, confirming details, and ensuring all necessary materials are available in advance.

• Support personal assistant duties such as coordinating household-related requests, managing gift purchases, and handling special arrangements for family needs.

• Track and process business expenses, maintain accurate records, and help ensure timely submission of reimbursements.

• Serve as a dependable point of coordination for time-sensitive requests, following through on details with discretion and confidentiality.


Requirements:

  • 10–15+ years of experience in a high-level Executive Assistant / Personal Assistant role
  • Proven expertise managing complex calendars and high-touch travel, including private jet coordination
  • Exceptional organizational, multitasking, and problem-solving skills
  • Strong emotional intelligence with the ability to work effectively with a reserved executive and family members
  • Comfortable handling sensitive personal matters with discretion and professionalism
  • Highly polished with a strong sense of ownership and accountability
  • Proactive, resourceful, and always thinking ahead
  • Flexible and available outside of standard business hours as needed


// // //