Chief Executive Assistant

Squared Away

Chief Executive Assistant at Squared Away handling complex schedules, communications, and travel logistics for senior executives. Required significant experience and availability during U.S.

Posted 6/30/2026contractRemote • Alabama, Alaska, Arizona, California, Colorado, Florida, Hawaii, Illinois, Iowa, Kentucky, Louisiana, Maryland, Missouri, Montana, North Carolina, Ohio, Pennsylvania, South Carolina, Tennessee, Texas, Virginia, Washington • 🇺🇸 United StatesLead💰 $24 - $36 per hourWebsite

About the role

Key responsibilities & impact

Manage and optimize complex executive calendars across time zones.
Anticipate conflicts and proactively resolve scheduling issues.
Protect executive focus by enforcing priorities and boundaries.
Manage executive inboxes with discretion and sound judgment.
Draft, respond to, and triage correspondence on behalf of executives.
Ensure urgent matters are surfaced promptly and appropriately.
Coordinate domestic and international travel end-to-end.
Prepare detailed itineraries and anticipate changes or disruptions.
Prepare meeting materials, agendas, presentations, and reports.
Track action items, deadlines, and follow-through across initiatives.
Create, document, and refine workflows to improve efficiency.
Identify tools and processes that reduce friction and increase clarity.
Conduct research on competitors, tools, vendors, and market trends.
Provide concise summaries to support executive decision-making.
Handle sensitive and confidential information with absolute integrity.

Requirements

What you’ll need

Applicants must maintain 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 living overseas on active orders are welcome to apply, provided they maintain a permanent address in one of the states listed above and can reliably support clients during U.S. business hours.
Must be available during normal business hours Monday–Friday, 9 AM–5 PM (in your time zone) for regular client communication.
Ability to commit a minimum of 20 hours per week, with flexibility to take on additional hours.
Administrative experience supporting senior leaders is required; experience supporting executive-level roles is strongly preferred.
Experience working remotely is strongly preferred.
Reliable home office setup, including:
Mac or PC computer with webcam
High-speed internet
Smartphone with email capabilities
A designated, quiet workspace suitable for professional work.
Strong written and verbal communication skills, able to clearly and concisely communicate in a variety of contexts.
Proficiency in Microsoft Office, including Word, Excel, PowerPoint, and Outlook, with familiarity using project management tools.
Experience managing schedules, communication, and priorities across time zones.
Understanding of cross-cultural communication in a global working environment.
Exceptional organization and attention to detail.
High emotional intelligence and situational awareness.
Comfortable working independently without constant direction.
Tech-savvy and quick to learn new systems and tools.
Proactive mindset that anticipates needs rather than reacts.

Benefits

Comp & perks

This is a fully remote 1099 independent contractor position.
Contractors are paid for billable hours worked.
Hourly rates determined by experience and tier level.
Tier 1: $24/hour
Tier 2: $30/hour
Tier 3: $36/hour
Contractors submit time through Harvest Time Tracking for billable work.
Payments are issued twice monthly.
Most contractors support 2–4 clients at a time.
Squared Away handles client acquisition, client contracts, billing, and invoicing.

ATS Keywords

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Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools

Calendar ManagementTravel LogisticsMicrosoft WordMicrosoft ExcelMicrosoft PowerPointMicrosoft OutlookProject Management ToolsResearch SkillsWorkflow DocumentationAction Item Tracking

Soft Skills

Attention To DetailEmotional IntelligenceSituational AwarenessProactive MindsetIndependent Work