Chief Executive Assistant – Generalist

Role Overview

• 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

• 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.