Military spouses who are your trusted assistants. We help CEOs, VCs, executives, and startup teams get their time back.

Chief Executive Assistant

Executive AssistantExecutive AssistantContractRemoteTeam 201-500Since 2018H1B No SponsorCompany Site LinkedIn

Location

New York

Posted

74 days ago

Salary

Not specified

English

Job Description

• 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.