Executive Assistant to the CEO

We are seeking an organized, proactive Executive Assistant who can manage multiple businesses and personal affairs for the CEO. This role requires exceptional coordination, strong communication, and the ability to anticipate needs in a fast-paced environment. The ideal candidate will be able to travel as needed, arrange travel, and handle a variety of administrative duties with discretion and reliability.

Position Overview

Support the CEO across multiple businesses and personal matters

Coordinate calendars, travel, and logistics to maximize executive productivity

Operate in a fast-paced, high-demand environment with a high level of confidentiality

Key Responsibilities

Calendar and Scheduling Management: efficiently manage five or more calendars simultaneously, prioritize commitments, and resolve scheduling conflicts

Travel Planning and Logistics: arrange flights, accommodations, ground transportation, and itineraries; optimize travel routes and manage expense reporting

Personal and Business Coordination: organize both professional and personal tasks to ensure seamless CEO operations across ventures

Communication Management: monitor and respond to emails, messages, and calls; act as a gatekeeper and liaison for internal and external stakeholders

Team Expansion and Staffing: assist in hiring and onboarding new support staff or contractors as needed for the CEO’s operations

Gatekeeping and Proactive Support: anticipate needs, prepare briefing materials, and provide four-dimensional thinking to foresee CEO requirements

Project and Task Management: track action items, follow up on decisions, and ensure timely completion of tasks

Document and Information Management: maintain organized digital filing systems; manage confidential information with discretion

Operational Readiness: maintain a high level of organization across multiple businesses and personal affairs

Qualifications

Proven experience as an executive or personal assistant supporting a CEO or high-level executive

Excellent organizational and time-management skills; able to manage multiple calendars and tasks concurrently

Strong travel planning expertise; comfortable arranging complex itineraries and travel logistics

Reliable transportation or access to dependable travel options as needed

Proficient in Google Suite (Docs, Sheets, Slides, Calendar, Drive) and strong general computer literacy

Outstanding communication skills (written and verbal)

High level of discretion and confidentiality; comfortable handling sensitive information

Resourceful and proactive thinker with the ability to anticipate CEO needs

Ability to work in a fast-paced environment and adapt to changing priorities

Hybrid work flexibility and willingness to travel as required

Work Environment

Hybrid: combination of remote work and in-person support as required

Travel as needed to support the CEO’s engagements

If this describes you, please prepare to copy and paste the following job description into a posting on Indeed.

Pay: $37,200.00 - $45,000.00 per year

Benefits:

• Flexible schedule

Work Location: Hybrid remote in Oak Park, IL 60301