Chief Executive Assistant

Squared Away; United States; Remote; USD 30,000 - 33,000; Full time

Job summary

Squared Away is seeking a senior-level Executive Assistant to support top executives in a fast-paced, high-expectation environment. You will manage calendars, communications, travel, and operational systems, delivering proactive support across multiple clients and time zones.

This is a fully remote position with a clear transition path from 1099 contractor in Q4 2026 to W-2 employment starting January 1, 2027.

Qualifications

• Administrative experience supporting senior leaders.
• Strong written and verbal communication.
• Must maintain a permanent U.S. address.
• Available 9 AM–5 PM in your time zone for regular client communication.

Responsibilities

• Manage complex executive calendars across time zones.
• Protect executive focus by enforcing priorities.
• Draft, respond to, and triage correspondence for executives.
• Coordinate domestic and international travel end-to-end.
• Prepare meeting materials, agendas, presentations, and reports.
• Track action items, deadlines, and follow-ups across initiatives.
• Create, document, and refine workflows to improve efficiency.

Skills

Executive support

Schedule management

Communication

Remote work experience

Tools

Microsoft Office

Job description

Squared Away supports founders, executives, and leadership teams moving fast, carrying a lot, and expecting excellence.

Our Assistants are not task-takers waiting for instructions. They are strategic operators, problem-solvers, and trusted partners who create order in the chaos, anticipate what’s coming next, protect priorities, and make sure nothing important gets dropped.

We exist to give exceptional leaders back their most valuable resource: time.

That requires more than checking boxes. It requires judgment, discretion, ownership, extreme attention to detail, and the ability to execute consistently in environments where the pace is high and the expectations are higher.

If you need someone to tell you exactly what to do next, this probably isn’t the role for you.

If you are the person who notices the problem before anyone else does, figures it out, communicates clearly, and gets it across the finish line, we want to know you.

Squared Away maintains a rolling application for our Executive Assistant position. This application is for opportunities anticipated during Q4 2026, (October through December).

A Note About Our 2027 Transition

Squared Away is transitioning its Chief Executive Assistant team to W-2 employment beginning January 1, 2027.

Candidates who join Squared Away during Q4 will initially onboard as 1099 independent contractors for the remainder of 2026. Effective January 1, 2027, they will transition to W-2 employment with Squared Away, along with the rest of our Chief Executive Assistant team.

Compensation, availability expectations, and other employment terms change with the transition to W-2 employment. Both the Q4 contractor terms and 2027 W-2 terms are outlined below so candidates can understand the full opportunity before applying.

We are looking for candidates who are interested in building a longer-term career with Squared Away and are prepared to transition to the W-2 position in January.

What We’re Looking For

This is not an entry-level role, and it is absolutely not a side gig.

As a Chief Executive Assistant at Squared Away, you will work alongside senior executives who move quickly, manage significant responsibility, and expect the person beside them to think ahead, communicate clearly, and execute without needing constant direction.

You will manage competing priorities, anticipate needs before they become urgent, protect your executive’s time, and take ownership of outcomes at a level that mirrors exceptional in-house executive support.

We are looking for experienced professionals who know how to operate in ambiguity, solve problems without waiting to be rescued, exercise strong judgment, and build trusted relationships with high-performing leaders.

You should be comfortable making decisions, asking smart questions, following through relentlessly, and owning your work from start to finish.

This role is for someone who does not just want to support an executive. It is for someone who wants to become indispensable to one.

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
• Communicate clearly when priorities, deadlines, or circumstances change
• Build systems and routines that allow them to manage multiple priorities without sacrificing quality
  

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)

• Applicants must maintain a permanent U.S. address in one of the following states:
• Alabama, Alaska, Arizona, California*, Colorado, Florida, Georgia, Hawaii, Illinois*, Indiana, Iowa, Kentucky, Louisiana, Maryland*, Michigan, Missouri, Nevada, North Carolina, Ohio, Pennsylvania*, South Carolina, Tennessee, Texas, Virginia, Washington*.
• Local hiring restrictions apply in the following areas:
  • California: We are not currently hiring individuals whose primary work location is within Berkeley, Emeryville, Los Angeles, Oakland, San Francisco, Santa Monica, or West Hollywood.
  • Illinois: We are not currently hiring individuals whose primary work location is within Chicago or Cook County.
  • Maryland: We are not currently hiring individuals whose primary work location is within Montgomery County.
  • Pennsylvania: We are not currently hiring individuals whose primary work location is within Pittsburgh.
  • Washington: We are not currently hiring individuals whose primary work location is within Seattle.
    

Military spouses living overseas on active orders are welcome to apply, provided they maintain a permanent address in one of the states listed above and can reliably support clients during U.S. business hours.

• 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 50 hours per month, with flexibility to take on additional hours
• Administrative experience supporting senior leaders is required; experience supporting executive-level roles is strongly preferred.
• 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 & 2027 Transition

Candidates hired during Q4 will begin as 1099 independent contractors through December 31, 2026 and transition to W-2 employment effective January 1, 2027.

October–December 2026: Independent Contractor

All new Chief Executive Assistants begin at Tier 1: $24/hour.

Beginning January 1, 2027: W-2 Employment

Effective January 1, 2027, the Tier 1 rate is $22/hour.

W-2 hourly rates reflect the shift from independent contractor status to employment, including employer-paid payroll taxes and the benefits provided as part of the W-2 employment package.

How the Role Works

• Assistants are paid for hours worked.
• Time is tracked through Harvest Time Tracking, and payments are issued twice monthly.
• Most assistants support 2–4 clients at a time.
• Client assignments are based on business needs, availability, experience, and fit.
• Squared Away handles client acquisition, client contracts, billing, and invoicing so you can focus on providing exceptional executive support.
• You’ll work with a vetted client base across a wide range of industries, including venture capital, consulting, finance, marketing, nonprofit, real estate, technology, and more.
• This is a fully remote role.

Beginning January 1, 2027, assistants will become W-2 employees and will be eligible for the policies and benefits applicable to the W-2 Chief Executive Assistant position.

Candidates who move forward in the hiring process will receive information about the full 2027 employment package before accepting an offer.

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.

Privacy Notice

By applying, you acknowledge and agree to our Candidate Privacy Notice.