Pros
You get loads of autonomy and influence over product and design. You won't be a code monkey.
Cons
This can be very very inconsistent depending on the team. In my experience I encountered clueless managers trying to further their own careers over the betterment of the team. There are quite a few living embodiments of the Dunning-Kruger effect! The environment started feeling a lot more corporate. The classic issues of 'waterfall masquerading as agile' have started to crop up. The number of meetings kept going up and don't expect to get any concentrated time to do work as Slack will ensure you're constantly distracted! The company is also in a bit of an identity crisis about what the product actually is. Ask 10 people and you'll get 10 different answers. None of them incorrect but not entirely correct either. The culture and values on paper look great but I'm finding it harder and harder to see those values in a practical way. It doesn't matter what you write on the wall but what you reward and who you promote. In my experience there was a massive incongruity between the written values and practical values. There is a certain kind of person that can succeed at TransferWise. The traits likely to do well are over confident, loud, loves to talk and can make themselves heard in a loud meeting. It's rather sad because here's a company that has literally everything going for it. It's solving a real problem with a product that seems to work (so far) and is profitable. The management seem to be caught like a rabbit in the headlights though and that could cripple the company's long term prospects.
