Pros
The company has evolved a lot over the years and I think it's in a really great place right now. I'm happy whenever I'm working on interesting projects with people I respect - I think I got really lucky in that regard by coming to Dropbox. This is still a place for engineers with energy and drive to do great things. The size of our infrastructure and technical challenges is much higher than people expect. I could be working on infra basically any company in the world right now, but I feel like I have the highest leverage and direct impact at Dropbox than at any alternative.
Cons
It's still a growing company and we need to keep scaling the organization. How well will we handle having remote offices, or more of an org chart, or scaling communications as the company gets big? No real problems right now, but it's still a work in progress. (This is something I enjoy by the way.)