Pros
99designs office looks funky and unique. It does create an environment that's fun and comfortable to work in. The CEO is amazing, down to earth and makes the effort to get to know everyone. He hangs out with us and is active to be present in any event we have. He is genuine and he is smart. He works hard and he networks well. Everyone loves him. He has brought the company to new levels and everyone seems motivated to strive for the best. The company cares about the users very much. 99designs is always trying to improve their site to not only meet business goals but to help their users achieve personal goals.
Cons
The unfortunate thing is that they don't hire good managers to support the team. They are not clear with what they want, how they want to improve their product and how to achieve the goals. They are easily swayed by subjectivity and have very weak organisational skills. Senior management are always not at work but they want to micromanage when they are around. They turn out to be roadblocks and yet want to take credit for everything, instead of giving credit to the team. The culture isn't healthy. There are a lot of cliques, and they are not open and welcoming as they put out to be. People make racist remarks and there are a lot of biases given to the popular staff members. Some people are ignored and some people are judged for how they behave, if they are not 'in' the crowd. Swearing seems to be the norm which I think it's ignorant and unpleasant. Social activities are not diverse, not to mention they involve elicit drugs. Even though it's been reported, they do nothing about them.