Squared Away Reviews

3.2

50% would recommend to a friend

(140 total reviews)
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Michelle Penczak

52% approve of CEO

43% positive business outlook

Squared Away has an employee rating of 3.2 out of 5 stars, based on 140 company reviews on Glassdoor which indicates that most employees have a good working experience there. The Squared Away employee rating is in line with the average (within 1 standard deviation) for employers within the Human resources and staffing industry (3.8 stars).

Reviews by job title

140 reviews
4.0
15 June 2026
Recommend
CEO approval
Business outlook

Pros

flexible job, great for families

Cons

I have none at this time.

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Squared Away Response
1w
Thank you for taking the time to leave a review and for sharing your experience with Squared Away. We're glad to hear that the flexibility of the role worked well for you and your family. Creating opportunities that support military spouses, parents, and professionals with busy lives has always been an important part of our mission. We appreciate your support and wish you continued success in whatever comes next.
1.0
9 June 2026
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.

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Squared Away Response
2w
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.
1.0
8 June 2026
Recommend
CEO approval
Business outlook

Pros

Working from home part is great!

Cons

Everything! Would not recommend working for this company.

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Squared Away Response
2w
Thank you for sharing your feedback and for highlighting the flexibility that remote work can provide. We're sorry to hear that your overall experience did not meet your expectations. While this review does not include specific examples that we can meaningfully address, we recognize that not every workplace is the right fit for every individual. At Squared Away, we continually evaluate our policies, processes, and business model to support both our clients and our team members while building a sustainable organization for the future. We appreciate the time you spent with us and wish you success in your next opportunity.
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Glassdoor has 180 Squared Away reviews submitted anonymously by Squared Away employees. Read employee reviews and ratings on Glassdoor to decide if Squared Away is right for you.