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Squared Away Jobs (NOW HIRING)

Squared Away

Chief Executive Assistant

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 ...

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Squared Away information

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$31K

$36.3K

$50.5K

How much do squared away jobs pay per year?

As of Sep 3, 2026, the average yearly pay for squared away in the United States is $36,260.00, according to ZipRecruiter salary data. Most workers in this role earn between $33,500.00 and $34,000.00 per year, depending on experience, location, and employer.

What is a Squared Away assistant?

Squared Away assistants are remote executive assistants who provide administrative, organizational, and operational support to businesses and professionals. They help with tasks such as scheduling, email management, research, travel arrangements, and project coordination. Squared Away hires skilled military spouses and veterans for these positions, leveraging their discipline and adaptability. Clients work with dedicated assistants to streamline their workflow and focus on core business activities.

What are the key skills and qualifications needed to thrive as a virtual assistant at Squared Away?

To thrive as a Virtual Assistant at Squared Away, you need excellent organizational skills, attention to detail, and proficiency in administrative tasks, often supported by prior administrative or executive assistant experience. Familiarity with productivity tools like Google Workspace, Slack, Zoom, and project management platforms such as Asana or Trello is typically required. Strong communication, time management, and problem-solving abilities help you stand out in this remote, client-focused role. These skills are critical for efficiently supporting clients, managing diverse tasks, and ensuring smooth business operations from a virtual environment.

What are some common challenges virtual assistants at Squared Away might face, and how can they effectively overcome them?

Virtual assistants at Squared Away often encounter challenges such as juggling multiple client priorities, adapting to diverse work styles, and maintaining clear communication across time zones. Successfully managing these challenges requires strong organizational skills, proactive time management, and frequent check-ins with clients to clarify expectations. Building a habit of using digital tools for task tracking and maintaining open lines of communication with both clients and the internal team can greatly enhance efficiency and job satisfaction.

What is the difference between Squared Away vs Bookkeeper?

AspectSquared AwayBookkeeper
Required credentialsBasic accounting knowledge, possibly some certificationsHigh school diploma, certification like QuickBooks certification often preferred
Work environmentRemote or small business settingsOffice-based, small to medium businesses
Industry usageFinancial services, consulting, small business supportAccounting firms, small business finance departments
Common search intentHow to manage personal or small business finances efficientlyHow to record financial transactions and maintain books

Squared Away typically refers to financial management services or tools aimed at personal or small business finance organization, often emphasizing budgeting and financial planning. Bookkeepers focus on recording financial transactions, maintaining accurate financial records, and ensuring compliance. While both roles involve financial data, Squared Away is more about overall financial health, whereas bookkeepers handle day-to-day bookkeeping tasks.

More about Squared Away jobs

What states have the most Squared Away jobs?

States with the most job openings for Squared Away jobs include:

What job categories do people searching Squared Away jobs look for?

The top searched job categories for Squared Away jobs are:

Squared Away jobs near you
Infographic showing various Squared Away job openings in the United States as of August 2026, with employment types broken down into 1% As Needed, 75% Full Time, 20% Part Time, and 4% Contract. Highlights an 85% Physical, 1% Hybrid, and 14% Remote job distribution, with an average salary of $36,260 per year, or $17.4 per hour.

Chief Executive Assistant

Squared Away

Remote

Contractor

This job post has expired today. Applications are no longer accepted.

Job description

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 Q3 2026 (July - September)
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.
Requirements
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.
      • 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 20 hours per week, 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

Benefits
Compensation & Contractor Details
  • This is a fully remote 1099 independent contractor position.
  • Contractors are paid for billable hours worked, with hourly rates determined by experience and tier level:
    • Tier 1: $24/hour
    • Tier 2: $30/hour
    • Tier 3: $36/hour
  • Contractors submit time through Harvest Time Tracking for billable work completed during each client plan period, and payments are issued twice monthly.
  • Most contractors support 2-4 clients at a time. Client opportunities are offered based on business needs, and contractors decide which opportunities to accept, allowing them to build a workload that aligns with their availability and business goals.
  • 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 with the flexibility to build a client portfolio that fits your schedule.

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
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