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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 – Generalist
Location
New York
Posted
118 days ago
Salary
$1.4K - $4K / month
Seniority
Lead
Job Description
Chief Executive Assistant – Generalist
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
- This is a contractor (1099) role with a revenue-sharing model.
- Assistants earn 60% of the monthly client plan value for each client they support.
- Most assistants support 2–4 clients at a time, with each client on a different plan level. Because of this, earnings vary based on the mix of clients and plans an assistant chooses to take on and may fluctuate month to month.
- In practice, most assistants earn between $1,440–$4,000 per month, with opportunities to earn more based on client volume, plan levels, and tenure.
- Earnings may vary outside this range depending on client mix, with higher-tier or multiple clients increasing total earnings.
- Assistants have full control over how many clients they support, their workload, and their schedule. There is no minimum or maximum number of hours required, and earnings scale accordingly.
- Squared Away manages client acquisition, billing, and invoicing so you can focus on client work. You'll have access to a vetted client base across industries including consulting, marketing, nonprofit, finance, real estate, and more.
- This is a fully remote role with flexibility in client load.
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