Chief Executive Assistant

This is a fully remote position, open to applicants in Alabama, +22 more states.

📋 Description

• Oversee and enhance intricate executive calendars across various time zones

• Anticipate scheduling conflicts and proactively address any issues

• Safeguard executive focus by maintaining priorities and boundaries

• Manage executive inboxes with discretion and sound judgment

• Draft, respond to, and triage communications on behalf of executives

• Promptly and appropriately highlight urgent matters

• Coordinate comprehensive domestic and international travel arrangements

• Create detailed itineraries and foresee potential changes or disruptions

• Prepare meeting materials, agendas, presentations, and reports

• Monitor action items, deadlines, and ensure follow-through on initiatives

• Develop, document, and refine workflows to enhance efficiency

• Identify tools and processes that minimize friction and enhance clarity

• Research competitors, tools, vendors, and market trends

• Provide concise summaries that aid executive decision-making

• Handle sensitive and confidential information with the utmost integrity

• Support assigned clients and build momentum during the initial 90 days

• Foster trust and rapport with executives through consistent communication and follow-through

• Cultivate an understanding of executive priorities, preferences, and work styles

• Establish reliable systems for tracking tasks, deadlines, and follow-ups

• Structure the workday to balance availability, focused work time, and responsiveness

⛳️ Requirements

• Must have a permanent U.S. address in Alabama, Alaska, Arizona, California, Colorado, Florida, Georgia, Hawaii, Illinois, Indiana, Iowa, Kentucky, Louisiana, Maryland, Michigan, Missouri, Nevada, North Carolina, Ohio, Pennsylvania, South Carolina, Tennessee, Texas, Virginia, or Washington

• Local hiring restrictions apply in specific areas of California, Illinois, Maryland, Pennsylvania, and Washington

• Military spouses residing overseas on active orders must maintain a permanent address in an eligible state and reliably support clients during U.S. business hours

• Availability required Monday–Friday, 9 AM–5 PM in the applicant’s time zone

• This role cannot be combined with another job that restricts availability during those hours

• Must be able to commit to at least 50 hours per month, with the flexibility to take on additional hours

• Required administrative experience supporting senior leaders

• Preferred experience in supporting executive-level roles

• Strongly preferred experience in remote work environments

• Must have a reliable home office setup, including a Mac or PC computer, webcam, high-speed internet, smartphone with email capabilities, and a designated quiet workspace

• Strong written and verbal communication skills are essential

• Proficiency in Microsoft Office, including Word, Excel, PowerPoint, and Outlook

• Familiarity with project management tools is advantageous

• Experience in managing schedules, communications, and priorities across 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 are required

• Ability to work independently without constant supervision

• Must be tech-savvy and quick to learn new systems and tools

• Proactive mindset that anticipates needs is essential

🏝️ Benefits

• 1099 independent contractor status through December 31, 2026

• Transition to W-2 employment effective January 1, 2027

• Employer-paid payroll taxes included as part of W-2 employment

• Benefits provided within the W-2 employment package

• Payment is issued twice monthly

• Fully remote position

• Client acquisition, contracts, billing, and invoicing managed by Squared Away

• Access to a vetted client base across various industries

• Eligibility for applicable W-2 Chief Executive Assistant policies and benefits starting January 1, 2027