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 forQ2 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.

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.

What You’ll Be Responsible For

Executive Operations & Time Management

Manage and optimize complex executive calendars across time zones
Anticipate conflicts and proactively resolve scheduling issues
Protect executive focus by enforcing priorities and boundaries

Executive Communication

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

Travel & Logistics

Coordinate domestic and international travel end-to-end
Prepare detailed itineraries and anticipate changes or disruptions

Preparation & Execution

Prepare meeting materials, agendas, presentations, and reports
Track action items, deadlines, and follow-through across initiatives

Systems & Process Improvement

Create, document, and refine workflows to improve efficiency
Identify tools and processes that reduce friction and increase clarity

Research & Strategic Support

Conduct research on competitors, tools, vendors, and market trends
Provide concise summaries to support executive decision-making

Financial & Bookkeeping Support (When Applicable)

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, or finance teams

Discretion & Trust

Handle sensitive and confidential information with absolute integrity

What Success Looks Like in the First 90 Days

In the first 90 days, successful Chief Executive Assistants at Squared Away typically:

Actively take on client work and build momentum by supporting assigned clients successfully
Build trust and rapport with their executive(s) through consistent communication and follow-through
Develop a strong understanding of executive priorities, preferences, and working style
Take ownership of calendar and inbox management, proactively anticipating needs and resolving issues before escalation
Establish reliable systems for tracking tasks, deadlines, and follow-ups
Communicate clearly and confidently, even when priorities shift or information is incomplete
Maintain discretion and professionalism while handling sensitive information
Structure their workday to balance availability, focused work time, and responsiveness

This is not about perfection. It’s about progress, ownership, and building momentum.

Minimum Qualifications (Required)

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 of20 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

Skills & Attributes We Look For

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

Additional Experience That May Be Helpful

Experience with QuickBooks, Xero, or similar tools
Experience supporting bookkeeping or financial operations
Strong comfort working with numbers and financial documentation
High level of attention to detail and accuracy

Compensation & Contractor Details

This is a contractor (1099) role with a revenue-sharing model.
Assistants earn60% of the monthly client plan value for each client they support.
Most assistants support 2–4 clients at a time, with each client on a different plan level. Because of this, earnings vary based on the mix of clients and plans an assistant chooses to take on and may fluctuate month to month.
In practice, most assistants earn between$1,440–$4,000 per month, with opportunities to earn more based on client volume, plan levels, and tenure.
Earnings may vary outside this range depending on client mix, with higher-tier or multiple clients increasing total earnings.
Assistants have full control over how many clients they support, their workload, and their schedule. There is no minimum or maximum number of hours required, and earnings scale accordingly.
Squared Away manages client acquisition, billing, and invoicing so you can focus on client work. You’ll have access to a vetted client base across industries including consulting, marketing, nonprofit, finance, real estate, and more.
This is a fully remote role with flexibility in client load.

Authentic, not Artificial

We value clear thinking, sound judgment, and authentic communication.

We recognize that AI tools are increasingly part of how people work, and we support thoughtful, responsible use of them.

During the application process, we’re looking to understand howyou think and communicate. Responses should reflect your own voice, experience, and decision-making. Submitting answers that are fully generated by AI, without your input or perspective, may impact your candidacy.

If you move forward, it’s because we see how you approach problems, communicate under pressure, and make decisions. We’re not looking for perfection; we’re looking for clarity, ownership, and professionalism.

Reapplying?

If you’ve applied previously and were not selected, we encourage you to reapply. We release updated versions of this application each quarter to reflect evolving needs and give returning candidates another opportunity to be considered.

Privacy Notice

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Squared Away remote jobs

Chief Executive Assistant

Chief Executive Assistant (Marketing & Growth Focus)

Chief Executive Assistant (Bookkeeping-Focused)

Chief Executive Assistant (Generalist)