Chief Executive Assistant (Generalist)

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 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 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

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 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

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

Compensation & Contractor Details

• This is a contractor (1099) role with a revenue-sharing model.
• Assistants earn 60% 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 how you 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.