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A Company Moving in the Wrong Direction - Executive Assistant Squared Away Employee Review

1.0

9 Jun 2026

Executive assistant

Recommend

CEO approval

Business outlook

Pros

The primary benefit of this company is the exposure to successful clients and growing businesses. For contractors, it can provide valuable networking opportunities and the chance to build relationships that may evolve into direct working arrangements once a contract buyout is completed. Personally, my buyout experiences resulted in the best working relationships I found during my time with the company.

Cons

The biggest drawback of working with this company is the disconnect between leadership and the contractors who actually perform the work. Throughout my time with the company, I often felt that decisions were made with little consideration for the impact they would have on assistants and account managers. The company promotes values such as transparency, support for working parents, and an open-door policy. Unfortunately, my experience did not reflect those values. When concerns were raised regarding leadership decisions, feedback was often met with resistance rather than meaningful discussion. Employees and contractors who questioned policies frequently felt dismissed, and opportunities for open dialogue seemed limited. One of the most concerning issues involved changes to contractor compensation. The agreement I signed stated: "The Contractor will receive 60% of the total fees collected from clients for services rendered, while 40% will be retained by Squared Away Partners, LLC as an administrative fee." For years, this was understood and applied as contractors receiving 60% of the total client plan value. More recently, leadership reinterpreted this language to mean payment based only on hours used by the client rather than the total fees collected. This represented a significant change in compensation and created confusion and frustration among contractors who had relied on the original structure. The communication surrounding these changes further contributed to instability. Contractors were left fielding questions from clients while trying to understand policy changes themselves. Rather than creating confidence, the process left many people uncertain about their role, compensation, and future with the company. While there are some talented people within the organization who genuinely care about clients and contractors, I believe leadership decisions have negatively impacted company culture, trust, and long-term growth. Prospective contractors should carefully review compensation terms, ask detailed questions about pay structure, and ensure they fully understand how compensation is calculated before joining.

Squared Away Response

Thank you for taking the time to share your experience and for recognizing the opportunities that Squared Away can provide through exposure to clients, professional growth, and long-term networking relationships. We are genuinely proud that many of those connections continue well beyond a contractor's time with our company. We also recognize that periods of operational change can be difficult. As our business has evolved, we have had to make decisions that were intended to create a more sustainable model for both our clients and the company itself. We understand that not everyone agrees with those decisions, and we respect that people can walk away with different perspectives. As a matter of principle, we do not publicly engage in personal criticisms of individual leaders or team members. We believe those conversations are best left out of professional forums, and we prefer to focus on the policies and business decisions that shape the contractor experience. With respect to compensation, our goal has always been to create a structure that aligns payment with services delivered to clients. We understand that changes affecting compensation are significant, and we know they can be frustrating, particularly for those who had become accustomed to a different operational model. We also agree that trust, communication, and consistency matter. They are not just recruiting concepts; they are things every organization has to work at continuously, especially during times of change. While we may not share every conclusion in this review, we appreciate the time and thought that went into writing it, and we will continue working to build a company that supports both the people who serve our clients and the clients who place their trust in us. We sincerely wish you success in your future endeavors.

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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.

Squared Away Response

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

Administrative assistant

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.

Squared Away Response

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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A Company Moving in the Wrong Direction - Executive Assistant Squared Away Employee Review

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