Pros
There were (and still are) some really awesome, smart people there. Despite the many cons, the employees all really enjoyed working together. Good camaraderie and lots of fun times in the office. I have many friends and good memories from my time there. Their new office is beautiful, too bad it's near empty now. Good office snacks, benefits package, Nice Days (PTO days you can use without notice any time for any reason), and a nice product. Work/life balance was pretty great, and most managers were pretty flexible to allow WFH when needed.
Cons
Pretty severely mismanaged business, resulting in tons of turnover and many layoffs (even before COVID). As many others have already said, unfortunately a lot of this comes down to the CEO. Next-level micromanagement plus awful (and disrespectful) time management created constant bottlenecks. He will go out of his way to avoid uncomfortable decisions or conversations even if you are waiting for a decision or approval from him. He cannot accept the fact that other people in the business (that he hired!) might know more than him in certain functions. He wants things a certain way, but at the same time usually can't articulate what that way is—only what it isn't. So as a result, you spend time doing work that gets sent back time and time again. Sadly, he has no trust in his employees to just do their best work. While there was potential for a great culture, it was obvious to everyone that it was more important that we project a facade of this amazing culture without actually spending the time to build it. Our image was far more important than our actual experience - ironic, for an experience-focused company/product. The "company values" are completely made up and have no substance behind them. They are just cutesy words. There was little to no career advancement opportunity. We heard for months that a "career ladder" plan was in the works, but never saw the light of day. Constant pivots in product and target market made it very difficult to gain traction or have any kind of momentum. Sales suffered because of this. Finally, for a company that talks so much about customer experience, it felt like our own customer experience was not at the top of the priority list. The whole company can see our customer feedback as it comes in, and negative feedback was rarely addressed or incorporated unless it came from one of our top moneymakers. This was especially aggravating when we would see the same type of complaints come in over and over again. Our CSMs did a wonderful job supporting our customers as best they could, but they were overworked and undersupported.