Remote Chief Executive Assistant & Strategic Partner

Squared Away; United States; Remote; USD 33,000 - 50,000; Full time

Job summary

Squared Away is seeking a Chief Executive Assistant to support senior executives as a trusted, proactive partner in a remote 1099 role.

You will manage calendars across time zones, coordinate complex travel, prepare materials, and streamline systems, while upholding confidentiality and high standards.

This role emphasizes ownership, thoughtful communication, and the ability to adapt as priorities evolve, with flexible hours and client-focused work.

Qualifications

• Administrative experience supporting senior leaders is required; experience supporting executive-level roles is strongly preferred.
• Must be available during normal business hours Monday–Friday 9 AM–5 PM in your time zone.
• Ability to commit a minimum of 20 hours per week, with flexibility to take on additional hours.
• Remote work strongly preferred.

Responsibilities

• Executive Operations & Time Management: Manage and optimize complex executive calendars across time zones; anticipate conflicts and proactively resolve scheduling issues; enforce priorities and boundaries.
• Executive Communication: Manage executive inboxes with discretion and sound judgment; draft, respond to, and triage correspondence; surface urgent matters promptly.
• Travel & Logistics: Coordinate domestic and international travel end-to-end; prepare detailed itineraries and anticipate changes.
• Preparation & Execution: Prepare meeting materials, agendas, presentations, and reports; track action items, deadlines, and follow-ups.
• Systems & Process Improvement: Create, document, and refine workflows to improve efficiency; identify tools and processes that reduce friction.
• Research & Strategic Support: Conduct research on competitors, tools, vendors, and market trends; provide concise summaries to support executive decision-making.
• Discretion & Trust: Handle sensitive information with absolute integrity.

Skills

Executive support

Calendar management

Time management

Communication

Discretion

Tools

Microsoft Office

PM tools

Job description

Squared Away is seeking a Chief Executive Assistant to support senior executives as a trusted, proactive partner in a remote 1099 role.

You will manage calendars across time zones, coordinate complex travel, prepare materials, and streamline systems, while upholding confidentiality and high standards.

This role emphasizes ownership, thoughtful communication, and the ability to adapt as priorities evolve, with flexible hours and client-focused work.