Bullying Leadership - Chief Executive Assistant Squared Away Employee Review

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.

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.

-flexibility -resume building -client matching

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.