Chief Executive Assistant (Bookkeeping-Focused)

Squared Away

4h•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 all of our Executive Assistant position. This posting is for Q2 2026 (April - June) 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 executive support role first. However, Some of the executives we support require additional support with financial organization and bookkeeping-related workflows. We are particularly interested in candidates who have hands-on experience with bookkeeping tasks such as expense tracking, invoice management, and reconciliation, and who are comfortable working with financial data. This role is best suited for those with experience supporting bookkeeping or financial operations in a practical, execution-focused capacity. This is not an accounting role and does not include tax preparation or advisory responsibilities. Not sure this is the right fit? This role is designed for candidates with bookkeeping experience or exposure to financial workflows. If your background is more general, we encourage you to apply to our Executive Assistant (Generalist) role. Our team reviews candidates across all tracks, so applying to the role that best reflects your experience helps us evaluate you more effectively. This is an independent contractor role designed for experienced professionals who want flexibility without sacrificing standards.

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