Pros
I've worked in at many companies, in many different industries. This is far and away the best place I've worked. We provide a legitimately helpful, beneficial service to our clients, with no downside to anyone. My colleagues are some of the most intelligent, dynamic, kind people I've ever met. The culture is open, inclusive, not rigid at all.
Cons
Every medium-large company has a certain amount of bureaucracy. TransferWise is no different. But it has less of it than I've experienced before. People who need a ton of structure — who need to be told what to do to do their job — might struggle here. Being a self-starter is rewarded. Also there is not necessarily a steady, prescribed path to moving up. You move up if you do good work, but there's no formula (years + KPIs, for instance) that guarantees it. At least not that I've seen. I actually like that. I understand why some may not.