Squared Away

Chief Executive Assistant

Squared Away

contract

Posted on:

Location Type: Remote

Location: Remote • New York • 🇺🇸 United States

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Job Level

Lead

About the role

  • 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

  • Administrative experience supporting senior leaders is required; experience supporting executive-level roles is strongly preferred.
  • Must be based in a U.S. time zone (EST, CST, MST, or PST); applicants must reside in the United States, **excluding New York**
  • Must be available during normal business hours Monday–Friday, 9 AM–5 PM (in your time zone) for regular client communication
  • This role cannot be combined with another job that limits availability during these hours
  • Ability to commit a minimum of **20 hours per week,** with flexibility to take on additional hours
  • 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
  • Independent contractor (1099) role
  • Client payments are distributed on a **60/40 split**, with **60% paid directly to the assistant**
  • Assistants choose how many client hours they take on
  • Squared Away manages client acquisition, billing, and invoicing
  • Access to a vetted client base across industries including consulting, marketing, nonprofit, finance, real estate, and more
  • 100% remote with flexibility in client load
  • Earnings vary based on client plans, hours worked, and availability; assistants have control over their client load and overall monthly earnings.

Applicant Tracking System Keywords

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

Hard skills
administrative experiencescheduling managementcorrespondence draftingitinerary preparationworkflow documentationresearch skillsMicrosoft Officeproject management toolstime zone managementconfidential information handling
Soft skills
communication skillsorganizationattention to detailemotional intelligencesituational awarenessindependenceproactive mindsetdiscretionproblem-solvingflexibility