Chief Executive Assistant

Squared Away

23h • Remote

About The Position

Squared Away supports founders, executives, and leadership teams operating at a high level of complexity and pace. Our assistants are not task-takers. They are trusted, strategic partners who bring structure, clarity, and follow-through to demanding environments. We exist to give people their most valuable resource back: time. That work requires judgment, discretion, and consistency, every single day. Squared Away maintains a rolling application for our Executive Assistant position. This posting is for Q1 2026 (January - March) What We're Looking For This is not an entry-level role, and it is not a side role. As a Chief Executive Assistant at Squared Away, you will support senior executives who expect proactive thinking, excellent communication, and dependable execution. You will manage competing priorities, anticipate needs before they are voiced, and operate with a level of ownership that mirrors in-house executive support. This is an independent contractor role designed for experienced professionals who want flexibility without sacrificing standards. What Tends to Work Well in This Role Our work is fast-paced, collaborative, and built on trust. Assistants who thrive here typically: Have established experience supporting senior executives Enjoy variety and problem-solving over repetitive task work Are available and responsive during weekday business hours Take a proactive approach and anticipate needs rather than waiting for direction Stay effective when priorities change or when not everything is fully defined Treat confidentiality and discretion as non-negotiable Structure their day with dedicated work blocks in the morning and afternoon, allowing for consistent availability, focused work time, and timely communication with executives If you see yourself in this list, you’re likely a great match for how we work at Squared Away.

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

Responsibilities

• 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

Benefits

• 100% remote with flexibility in client load
• 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

What This Job Offers

• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 11-50 employees