Pros
The people. You will work with some awesome people who will become your friends. Spiceworks hires some of the smartest and nicest people I've met. Everyone looks out for one another and it's truly a team-first environment.
Cons
Even though you work WITH great people, you'll likely end up working FOR some bad managers. There's a lot of managers that should stick to individual contributor roles. They simply don't have the training to properly manage and mentor a team. Executive management is a joke ever since Scott left. In just over a year, the culture has shifted dramatically. It used to be truly a great place to work, but management has gone increasingly less transparent lately. There is too much emphasis on revenue first, quality product last. They scaled up the sales team without making sure the product was good, both IT and Marketing.