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Virtual Chief Executive Assistant – Reserved for Military Spouses

Squared Away
Remote - Overseas, Japan or, United States of America
Job Type


Fully Remote Chief Executive Assistant:

Squared Away is looking for a Virtual Chief Executive Assistant to work with our team. This person will work to support the daily operations of the clients they are matched with. We are fully remote and work U.S.-based timezones.

All applicants must be able to commit to at least 20 working hours per-week, between the hours of 9:00 am - 5:00 pm in U.S.-timezones.

Note: We are currently hiring for the January/February 2023 timeframe. We take the time to diligently screen and evaluate each individual candidate. If we do move forward with your application, you will be informed of how to access an earlier interview spot, as these earlier spots do open up regularly. If you do interview sooner than the current hiring time, please be prepared to start the role within a few weeks of your interview.

Overseas and Japan-based Applicants:

  • We do hire candidates who are stationed overseas (to include Japan). Japan-based business hours are rare. We do guarantee U.S.-based business hours (9:00 am - 5:00 pm EST, CST, MST or PST). For those based in Japan and similar locations, we welcome you to apply if you are willing to commit to U.S.-based business hours (working overnights from Japan).
  • Working from Japan or a similar overseas location is only permitted if you are on Government (PCS) orders.
  • From Japan or a similar location, you will be working part-time from approximately 11:00 pm - 7:00 am local time (WST). The 1-hour response time and 3-hour completion time for all Squared Away Chief Executive Assistants does apply for those working U.S.-based business hours from Japan.
  • If you are based in Europe or a nearby location, you should anticipate, and be able to commit to, working EST or CST U.S.-based business hours.

We are currently not registered in Delaware, Maine, Oregon, South Dakota, Vermont, and Wyoming. If we do offer you a position with Squared Away, and you are based out of (currently living in) any of these states, then your start date will likely be within 8-12 weeks of your interview. There is the potential for this date to be earlier than this, but we cannot guarantee an exact start date.

The ideal candidate is a proactive individual with excellent organizational skills, strong attention to detail, and the ability to communicate effectively in both written and verbal communications.


  • Proactively Assist the Client - Proactively plan for any situation that your client may face. This includes scheduling conflicts, project management, event planning, day to day operations management, and keeping the client's best interests in mind with all tasks.
  • Relationship building - We are here to support you to professionally build a relationship with your client if you need our help.
  • Email management - Actively manage email communications for the client.
  • Coordinate scheduling - Set up meetings based on cross-functional availability for both internal and external clients.
  • Facilitate executive-level operations - Book travel, submit expense reports, and send communications for the client as needed.
  • Team communication - We strive for open, honest communication about the areas you need support in. We have mentors within the team that are here to support you if you would like their help.


  • Minimum of 1-year experience in an administrative setting.
  • Must be available to work in any U.S. timezone.
  • A minimum of 1-year assistant experience is preferred.
  • Associates degree or higher is preferred for internal promotion opportunities. A high school diploma is a minimum requirement for applicants.
  • Bonus points for those with prior experience as Virtual Assistants or remote Chief Executive Assistant.
  • Experience in the following programs preferred: Slack, Google Drive, Microsoft Excel, Salesforce, Canva/Mailchimp and Quickbooks.
  • Embodies our four pillars: Over-communication, extreme attention to detail/proactivity, thinking outside of the box and being a team player.


This is a W-2 role. Our team has a percentage split of the client plan.

Teammates can take advantage of a flexible work environment with a community-like atmosphere. To have a better idea of when our team is most active, our team is generally online with their clients between 9:00 am - 5:00 pm in U.S.-timezones.

Company Culture:

Learn more about our team and our culture on Instagram, Twitter, LinkedIn, and Facebook.

About Squared Away:

We exist to make work better by letting our clients focus solely on what matters. We are our client's trusted assistants. This entire journey started because Michelle, our CEO & Co-Founder, couldn't get a job due to her being a military spouse. Constantly changing bases meant being in a different city at a moment's notice. Everywhere she went, she met others with the same story. Highly educated, ready to work, struggling to find a job, Military Spouses.

That's when Squared Away was born. To empower Miltary Spouses to have meaningful opportunities, be our client's trusted assistant, and work from anywhere.

Today, we work with some of the best companies, teams, and Venture Captial firms in the world in addition to top executives and freelancers.

We aren't Virtual Assistants, we are Chief Executive Assistants who are our client's most trusted team members. We are our client's right hand. We anticipate our client's needs and are proactive vs. reactive. This is why most Virtual Assistants or automated robot assistants don't work.

We work with our team in high growth and scaling businesses. We help our clients make growth happen by making sure they can focus on the things that matter: growth and people.

Sure, we might do things that an assistant would do. Travel, meetings, research, etc. Except, we do it better, and we do a lot more than that.

Our team is a family, we base our work on four pillars: Over-communication, Extreme Attention to Detail/Proactivity, Thinking Outside of the Box, Being a Team Player.

We are accepting applications from all states within the U.S. These are for W-2 positions.




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