Senior Executive Assistant & VIP Travel Lead

Addison Group; Chicago (IL); On-site; USD 65,000 - 90,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

401(k)

Job summary

Addison Group in Chicago is seeking an experienced Executive Assistant to provide high-level professional and personal support to a senior executive. This is not a traditional administrative position; you will balance executive support, personal assistance, travel logistics, scheduling, expenses, and special projects.

The ideal candidate is resourceful, comfortable with AI tools, and able to work independently in a fast-paced, technology-forward environment.

Qualifications

• 3–5+ years of experience in executive support or high-trust roles.
• Experience supporting a founder or senior executive preferred.
• Ability to work independently and manage multiple priorities.
• Excellent written and verbal communication skills.

Responsibilities

• Provide comprehensive executive and personal support while balancing multiple priorities in a fast-paced environment.
• Coordinate calendars, appointments, meetings, reservations, deliveries, and other commitments.
• Handle lifestyle and household-related requests and personal logistics.
• Arrange domestic and international travel with detailed itineraries.
• Track travel plans and develop alternatives as schedules change.
• Manage expense reports, receipts, and reimbursements.
• Conduct research and execute special projects with minimal direction.
• Assist with executive dinners, events, VIP experiences, and high-touch arrangements.
• Utilize AI and technology tools to improve efficiency and communication.

Skills

Executive support

Travel coordination

Discretion

Calendar management

AI tools proficiency

Communication

Tools

Concur/Expensify

Microsoft Office

Google Workspace

Job description

Addison Group in Chicago is seeking an experienced Executive Assistant to provide high-level professional and personal support to a senior executive. This is not a traditional administrative position; you will balance executive support, personal assistance, travel logistics, scheduling, expenses, and special projects.

The ideal candidate is resourceful, comfortable with AI tools, and able to work independently in a fast-paced, technology-forward environment.