Chief Executive Assistant

Squared Away

. Manage and optimize complex executive calendars across time zones .

Posted 10/2/2026contractRemote • United StatesLead💰 $7,200 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates strong administrative support capabilities for executive-level roles, including calendar management, communication, and travel coordination. Proficient in Microsoft Office and project management tools, with a focus on organization, attention to detail, and proactive problem-solving.

Highest-signal resume keywords

Executive Calendar ManagementStrong Written And Verbal CommunicationMicrosoft Office ProficiencyExperience Supporting Senior LeadersAttention To Detail

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Calendar ManagementTravel CoordinationCorrespondence DraftingWorkflow DocumentationProject Management Tools Familiarity

Soft Skills

Emotional IntelligenceSituational AwarenessProactive MindsetIndependent Work CapabilityBuilding Trust And Rapport

Tools & Technologies

Microsoft WordMicrosoft ExcelMicrosoft PowerPointMicrosoft OutlookHigh-Speed Internet

Industry Keywords

Cross-Cultural CommunicationRemote Work ExperienceExecutive-Level SupportTime Zone ManagementConfidential Information Handling

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
Surface urgent matters 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
Research competitors, tools, vendors, and market trends
Provide concise summaries to support executive decision-making
Handle sensitive and confidential information with absolute integrity
Support assigned clients and build momentum during the first 90 days
Build trust and rapport with executives through consistent communication and follow-through
Develop understanding of executive priorities, preferences, and working style
Establish reliable systems for tracking tasks, deadlines, and follow-ups
Structure the workday to balance availability, focused work time, and responsiveness

Requirements

What you’ll need

Maintain 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 specified areas of California, Illinois, Maryland, Pennsylvania, and Washington
Military spouses living overseas on active orders must maintain a permanent address in an eligible state and reliably support clients during U.S. business hours
Availability during Monday–Friday, 9 AM–5 PM in the applicant’s time zone
Cannot combine this role with another job that limits availability during those hours
Ability to commit a minimum of 50 hours per month, with flexibility to take on additional hours
Administrative experience supporting senior leaders required
Experience supporting executive-level roles strongly preferred
Experience working remotely strongly preferred
Reliable home office setup with a Mac or PC computer, webcam, high-speed internet, smartphone with email capabilities, and designated quiet workspace
Strong written and verbal communication skills
Proficiency in Microsoft Office, including Word, Excel, PowerPoint, and Outlook
Familiarity with 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
Ability to work independently without constant direction
Tech-savvy and quick to learn new systems and tools
Proactive mindset that anticipates needs

Benefits

Comp & perks

1099 independent contractor status through December 31, 2026
Transition to W-2 employment effective January 1, 2027
Employer-paid payroll taxes as part of W-2 employment
Benefits provided as part of the W-2 employment package
Payment issued twice monthly
Fully remote role
Client acquisition, contracts, billing, and invoicing handled by Squared Away
Access to a vetted client base across diverse industries
Eligibility for applicable W-2 Chief Executive Assistant policies and benefits beginning January 1, 2027