Vantaggi
There are a ton of smart, passionate engineers to work with. This is one of the reasons why I am still here.
Svantaggi
Work life balance as a manager is abysmal. It is not uncommon for you (and your peers) to work late nights and weekends or forego company holidays to meet deadlines. The company touts a successful "Virtual First" program where employees have the flexibility to work from everywhere, but in reality it is PST-first. If you don't live on the West Coast, expect to work through lunch, bathroom breaks, and well past 6 P.M. local time. Dropbox sets extremely unrealistic expectations about how many responsibilities you should be able to juggle at once, with several competing priorities all with deadlines at the same time. You will waste several hours per week doing busy work passed down by upper management. There are frequent pivots in strategy (as many have said, leadership is a revolving door) that introduce an enormous amount of thrash. Performance reviews are time consuming and arduous. It's not uncommon to be given additional engineers/teams with no additional support to the point where you're managing 10, 11, sometimes 12 engineers. You'll become a catch all for things nobody else wants to do, and yet Dropbox will refuse to hire the right people to fill these roles because they are trying to save money. Worst of all, as you take on new responsibilities you will still be expected to complete everything else in the same amount of time.