Great Mission, Poor Execution - Virtual Assistant Squared Away Employee Review

1.0
19 Feb 2021
Recommend
CEO approval
Business outlook

Pros

Being able to work remotely

Cons

I must first stay the negative comments are spot on! I want it to be noted that I am not here to bash but rather share my experience with SA. hat haSquared Away leadership embodies the part of the military community I hate so much. Cliquish! The favoritism is unreal. They speak of "having grace" and "being kind," but unfortunately, they do not practice what they preach. What you see on the public slack channels is not what happens behind closed doors. The directors and team leads have secret slack channels where they speak ill of others. It's incredibly unprofessional, and it also creates a toxic work environment. We are 1099 contractors but are treated as W2 employees. SA requires us to be online all day, but we are only paid for the hours we work. We are tasked with things that we are unable to clock time for, essentially working for free. Example: We have to check our SA email and Slack channel every hour. We must do check-ins with our team leads every week. We are required to update google documents when asked. Most recently, I've heard from a current contractor that they are required to update their client document every two weeks with the same information that is being asked in their check-ins. Not only is that redundant, but it is also a waste of time, time in which they are not being paid for. If you want to move up to a Team Lead position, you must attend all meetings and extras to be considered. They are asking you to work for free if you want to be considered for a promotion. Is that even legal? There is an option for clients to buyout an assistant's contract, but SA makes it virtually impossible for clients to do so. Clients would have to pay 6x their contracted amount. A 75h package comes with a buyout cost of $18,000. For a company claiming to help military spouses, they sure do make it impossible for assistants to grow with their client or any other company outside SA. Though they have growing numbers, they also have an extremely high turnover rate. I have former teammates tve gone through five and six team leads. Leadership just can't let go of control (micromanage). The CEO and Team leads keep track of the time we clock on SA's Harvest account they created for us. We must CC and BCC leadership on all low-hour emails, end of week, and month emails. If our client doesn't use his/her hours, they taunt you on slack, forcing you to do stuff that you might not be comfortable doing and accuse you of not being proactive enough. When maybe your client is just busy. They make us provide our login information for our client's LastPass account, which all directors and team leads can access. That is something that should be private between the client and assistant. They claim to have an open-door policy, but if you do speak up, you will be treated with passive-aggressive behavior. Despite having anonymous surveys every month or so, the same complaints are ignored, and assistants are met with "If you don't like it, you can leave attitude." Upper management should take constructive criticism and be willing to adjust policies to make employees (let's face it, that's what they are) want to stay. I can tell you my time at SA was super stressful. I did not feel comfortable speaking to any of the directors and had zero trust in my team lead. They should consider outsourcing an HR department so assistants have a safe haven when filing grievances.

Explore other reviews about Squared Away

5.0
18 Jun 2026
Anonymous contractor
Recommend
CEO approval
Business outlook

Pros

I’ve been with Squared Away for more than five years, and after reading the recent reviews, I feel like I’m looking at a completely different company than the one I’ve experienced. The primary criticism seems to be a compensation model change. What many reviewers conveniently leave out is that assistants were previously compensated for client time whether that time was actively used or not. The new model simply requires people to invoice for work actually performed. That’s not exploitation. That’s how most businesses operate.

Cons

The uncomfortable truth is that Squared Away’s biggest challenge has never been leadership, clients, or the market. It’s the culture that developed among portions of its workforce. Because Squared Away was founded to create opportunities for military spouses, it attracted many incredible people. It also attracted people who believed the company owed them something simply because they were military spouses. Over time, flexibility became an expectation instead of a privilege; accommodation became an entitlement instead of a benefit; accountability became something to resist rather than embrace. I’ve watched employees complain about clients while refusing to proactively support them. I’ve watched people criticize leadership decisions while taking little interest in the financial realities required to keep a business alive. I’ve watched individuals demand empathy, grace, and understanding while extending very little of those things to the company itself. The irony is that many of the people most loudly criticizing Squared Away have benefited from opportunities, flexibility, and support they would be unlikely to find elsewhere. Has leadership made mistakes? Of course. Every leadership team does. But the narrative that Squared Away is failing because of poor leadership is simply false. If anything, leadership spent too long trying to accommodate people who had no intention of being satisfied.

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Squared Away Response
1w
Thank you for sharing your experience and for being part of Squared Away for more than five years. We recognize that periods of change can bring out very different perspectives, and we appreciate hearing from team members who have experienced those changes firsthand. While not everyone will agree on every decision we make, our goal has always been to balance meaningful opportunities for military spouses and Veterans with the realities of operating a sustainable business that serves clients well. One thing we have learned over the years is that strong organizations require both support and accountability. We remain committed to fostering a culture where people can grow, contribute, and succeed while continuing to deliver exceptional service to our clients. Thank you for your long-term commitment to the company and for taking the time to share your perspective.
2.0
7 Jun 2026
Recommend
CEO approval
Business outlook

Pros

-flexibility -resume building -client matching

Cons

The CEO is rude and ineffective. She will delete Slack posts if you disagree with her opinions. Also, things change constantly. She says it's due to being bootstrapped but this is a 9 year old company that just never figured out how to operate. The changes to policy and pay are never ending and impossible to keep up with. Note that this is now an HOURLY wage job but if your clients don't use all of their hours, you are punished by not being paid for those hours. They tell you to just be more proactive.

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Squared Away Response
2w
Thank you for taking the time to share your perspective and for recognizing the flexibility, client matching process, and professional experience that Squared Away aims to provide. As a matter of principle, we do not publicly respond to personal attacks directed at individual team members or our CEO, as we believe professional discussions are most productive when they focus on policies, processes, and the employee experience. We understand that operating in a growing business environment means that policies and processes evolve over time. While change can be challenging, those adjustments are made to improve long-term sustainability, create greater transparency, and better align compensation with the work being performed. We also want to clarify that our compensation model is designed to pay for services delivered to clients. As with many client-service organizations, workload can vary based on client needs, and we encourage proactive communication and support so that team members can maximize opportunities within their assignments. We're grateful for the feedback regarding our leadership team and are pleased to hear that you had a positive experience with many of the managers you worked alongside. We wish you the very best in your future endeavors.
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