Pros
99designs is one of those rare places that combine what you always wanted to work with. In my case, in the intersection between creativity, design, innovation, and technology. At the same time, 99designs really lives and breathes one of its core values 'Put People First'. This value materializes when the company incentivizes every employee to keep learning new things and collecting the skillsets they need to thrive on their career, regardless if that career will be in 99designs or not. On tougher situations when the world was facing a natural disaster or when an employee would find out they (or a loved one) was sick, 99designs shows such true and wholeheartedly compassion that you instantly understand the mantra of putting people first. I'm leaving after 6 years on their ranks and will take learnings for life.
Cons
The team is spread out into 3 big offices: Oakland, Melbourne, Berlin. Although that gives you plenty of opportunities to travel and work from those amazing cities, it makes communication hard.