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:
Work Location: Hybrid remote in Oak Park, IL 60301
