Pros
I was a pretty early employee at DigitalOcean (~25) and worked in the senior management team for over 2 years. I most recently helped with product and people operations. I found working with Ben to be relatively easy - he gave me a lot of room to grow and learn. If you're someone who learns by doing, DigitalOcean is a good place and you'll have a lot of flex to take initiative and run with it. The company generates really great revenue for such a young business and the venture partners are world class.
Kontras
I can understand how less experienced folks might get frustrated working at DO as it's generally finding itself all around, however I'm not sure what you'd expect from a massively successful venture backed startup. If you're looking to be with world class mentors, DO is probably not the place for you - you need to excel at learning by yourself and growing yourself. The result of this can manifest as a perceived chaos and instability, in reality it's mostly rapid growth all around.