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Military spouses who are your trusted assistants. We help CEOs, VCs, executives, and startup teams get their time back.
Chief Executive Assistant
Location
New York
Posted
168 days ago
Salary
0
Seniority
Lead
Job Description
Chief Executive Assistant
Squared Away
• 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
Job 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.
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