Chief Executive Assistant

This is a fully remote position, open to applicants in Alabama, +21 more states.

📋 Description

• Oversee and enhance intricate executive calendars across various time zones.

• Anticipate scheduling conflicts and proactively address them.

• Safeguard executive concentration by establishing priorities and boundaries.

• Manage executive email accounts with discretion and sound judgment.

• Draft, reply to, and triage communications on behalf of executives.

• Ensure that urgent issues are identified and addressed promptly and appropriately.

• Coordinate all aspects of domestic and international travel.

• Create detailed itineraries and anticipate potential changes or disruptions.

• Prepare meeting materials, including agendas, presentations, and reports.

• Track action items, deadlines, and follow-ups across various initiatives.

• Develop, document, and refine workflows to enhance efficiency.

• Identify tools and processes that minimize friction and enhance clarity.

• Conduct research on competitors, tools, vendors, and market trends.

• Provide succinct summaries to aid in executive decision-making.

• Manage sensitive and confidential information with the utmost integrity.

⛳️ Requirements

• Candidates must have a permanent U.S. address in one of the following states:

• Alabama, Alaska, Arizona, California, Colorado, Florida, Georgia, Hawaii, Illinois, Indiana, Iowa, Kentucky, Louisiana, Maryland, Michigan, Missouri, North Carolina, Ohio, Pennsylvania, South Carolina, Tennessee, Texas, Virginia, Washington.

• Military spouses residing overseas on active orders are encouraged to apply, provided they maintain a permanent address in one of the aforementioned states and can reliably support clients during U.S. business hours.

• Availability during standard business hours Monday–Friday, 9 AM–5 PM (in your time zone) for consistent client communication is required.

• Must be able to commit to at least 20 hours per week, with the flexibility to take on additional hours.

• Prior administrative experience supporting senior leadership is essential; experience in executive-level support is strongly preferred.

• Experience in remote work is highly desirable.

• A reliable home office setup must include:

• Mac or PC computer with webcam.

• High-speed internet connection.

• Smartphone with email capabilities.

• A designated, quiet workspace appropriate for professional tasks.

• Strong written and verbal communication skills, capable of conveying information clearly and concisely in diverse contexts.

• Proficiency in Microsoft Office, including Word, Excel, PowerPoint, and Outlook, with familiarity in using project management tools.

• Experience managing schedules, communications, and priorities across different time zones.

• Understanding of cross-cultural communication in a global work environment.

• Exceptional organizational skills and attention to detail.

• High emotional intelligence and situational awareness.

• Comfortable working independently without constant supervision.

• Tech-savvy with the ability to quickly adapt to new systems and tools.

• Proactive mindset that anticipates needs rather than merely reacting.

🏝️ Benefits

• This position is a fully remote 1099 independent contractor role.

• Contractors are compensated for billable hours worked.

• Hourly rates are based on experience and tier level:

• Tier 1: $24/hour.

• Tier 2: $30/hour.

• Tier 3: $36/hour.

• Contractors log time via Harvest Time Tracking for billable work.

• Payments are processed twice a month.

• Most contractors manage 2–4 clients simultaneously.

• Squared Away oversees client acquisition, contracts, billing, and invoicing.