Squared Away

Chief Executive Assistant

Squared Away

contract

Posted on:

Location Type: Remote

Location: 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 & Tools
administrative experiencescheduling managementcorrespondence draftingitinerary preparationworkflow documentationresearch skillsMicrosoft Officeproject management toolstime zone managementconfidential information handling
Soft Skills
communication skillsorganizationattention to detailemotional intelligencesituational awarenessindependenceproactive mindsetdiscretionproblem-solvingflexibility