Wish the practice matched the concept - Lead Executive Assistant Squared Away Employee Review

1.0
1 Feb 2021
Recommend
CEO approval
Business outlook

Pros

Work from home. Decent training and resources.

Cons

1) Despite being a 1099 independent contractor, you are treated as an entry level employee and monitored to the point of diminishing employee efficiency. This micromanagement is labeled as necessary to ensure quality performance, but it is really just a way to monitor all actions. 2) The illusion of being a tight-knit "work family" who have one anothers' backs is a farse. The directors look out for themselves and if you are insubordinate you will be let go. 3) Despite a large percentage of the cost of the client's package being paid to the company, there is very minimal support. Team leads are utilized as a front line go-to for the assistants to reach out to for help, but anything confided to a team lead goes right to the directors. Negative input that shows an assistant not complying or doing anything that does not follow complete submission will result in termination or passive aggressive treatment. 4) Policy states that you must be available full-time for your clients. However, you will only be paid based on the time you are actually working. Asking about availability adjustments with your clients is forbidden. A true 1099 position would not have this restriction. 5) There is an option for your client to buy our your "contract" from Squared Away, but you are not allowed to bring it up to your client, and the cost is too high for most of them to feasibly be willing to pay. This seems to go against the Directors' and CEO's remarks about how the company is meant to be a means to a permanent position with your client's company and moving on will be celebrated. 6) There are hardly any incentives for assistants or Team Leads who exceed basic performance minimums. You are expected to ensure clients almost always increase or add to their plan, but you still recieve the same percentage of pay for the added time. 7) Team leads have an immense amount of responsibility, which continues to grow, but do not recieve pay equal to their efforts. This is touted as a great honorable position to aspire to, but that is just to make the perceived intrinsic value enough to make up for the minimal pay. 8) The concept of supporting military spouses and the female workforce is wonderful. If they practiced what they preached the company would be phenomenal. However, it falls short and the concern for the people is sorely lacking. There will be a veil of support that will finish as soon as you question authority or dispute any rule or treatment by a client. You are expected to suck it up if a client treats you poorly. You will not be matched thoughtfully with a client who is a good fit for you (unless you're very lucky), but will just be a cog in the machine to pump out more profit. The concern for the employees is just not there. If you are resilient and lucky enough to be paired with a wonderful client you may have a good experience. Just don't expect to be compensated according to the time you will truly spend working and being available.

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.

avatar
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.

avatar
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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