Flexible job that's great for families - 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.

The assistants are the best part of the company. I had the opportunity to work alongside many talented, hardworking people who genuinely cared about their clients and consistently went above and beyond to support them. The remote nature of the role also provides flexibility, and the exposure to different industries and executives can be valuable.

The company I joined is not the company I am leaving. Over the past year, leadership has made a series of decisions that have steadily eroded trust among both assistants and clients. Communication became increasingly top-down, transparency disappeared, and major changes were often presented as decisions that had already been made rather than conversations worth having. The most disappointing aspect was watching leadership lose sight of the fact that assistants and clients are the business. Instead of investing in retention and relationships, the company repeatedly chose short-term decisions that damaged both. Contractors were expected to absorb significant changes with little notice. Long-standing relationships between assistants and clients were treated as interchangeable despite the fact that those relationships are the primary reason many clients stay. In my experience, leadership dramatically underestimated the impact of disrupting those relationships. The final straw was watching clients receive abrupt transition notices while assistants who had spent months or years building trust with those clients were effectively cut out of the process. It demonstrated a fundamental misunderstanding of what clients are actually paying for. Morale among assistants has deteriorated significantly. Many of the strongest assistants have already left or are actively seeking opportunities elsewhere. The culture that once made the company special has largely disappeared.