Chief Executive Assistant; Bookkeeping-Focused

About Squared Away

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).

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.

• 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.

• 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

• Track and organize expenses, receipts, and financial records
• Assist with invoice tracking and follow‑ups
• Support reconciliation of transactions and documentation
• Prepare basic financial summaries for executive review
• Coordinate with accountants, bookkeepers,…