Pros
The culture and benefits here are unlike any other company. When you hire for core values that are not just business-related, you end up with so many genuine and kind-hearted employees who eventually become your family. Early days of Zappos really allowed individuals to progress and learn so much from their teams and leaders. There was a lot of trust and autonomy for such a large company. The company really prioritized employees' wellbeing over business goals, which was huge. They always look for ways to improve happiness from the team level all the way up to the company-wide level. It was one of the most companies that I ever worked for (and probably ever will). It was so hard to leave after so many years there, but I'm forever grateful for everything that I learned and the projects I had the fortune to work on. There are countless positives that outweigh the negative below.
Cons
It was heartbreaking to feel the culture and morale begin to unravel the deeper the company experimented with structural changes, the onset of the pandemic, and with the eventual loss of Tony. There were a lot of positives to the self-organized structure, but it also came with some negative consequences over time. It blurred the lines when it came to leadership, vision, strategy, etc. There was no North Star for too long. It felt like half of the company was invested in the self-organization experiment while the other half was trying to keep the company afloat. Since everyone was not "all-in", it led to the creation of silos and duplicated work which eventually created unnecessary tension between teams. When you form a marketplace that forces teams to "break even" on their budget while other departments aren't playing along, don't have budget or simply don't want to pay for services that were once free...it starts to disintegrate the culture. Teams used to bend over backwards to help each other out and collaborate together on projects. But once teams had to add monetary value to their work (with no proper marketplace training), it really plagued the collaborative spirit that the company once had. Leadership also fell apart. There was a lack of unified vision. Some tried to insert traditional hierarchy into a system that was meant to flatten that. Every department was doing their own thing instead of working in step together. There was also a lot of favoritism/politics that I never thought would plague Zappos in the way that it did. Again, there are countless positives that outweigh the negative when it comes to working here as an individual employee. However, I worry for the company in the bigger picture if they don't start to pull together and get back to collaborating as a family.