Pros
The benefits were extremely helpful and were a reason why I (and others) stayed for so long. Work from home Wednesdays and free food were a plus.
Cons
If you were on the sales side, then you most likely did not have a life. A typical day at Upwork was working 45-50 hours a week, eating lunch at your desk, dealing with multiple "cliques" at work, unprofessional management and not being able to take PTO because of unrealistic expectations from higher-ups. A lot of external hiring led to hardly any career opportunities for the sales teams. The management lacked the tools needed to support their teams. Favoritism was big at Upwork. If you didn't go to the happy hours or interacted with the team, you were seen as "not part of the culture". Within Large Accounts, Mid Market and BDRs, hardly anyone has hit their quota within the last 6 months (or even throughout 2019). Don't just take my word for it, do your research on Linkedin and see how high the turnover has been within their sales department this year.