Pros
Relaxed dress code and environment; ability to work from home; good healthcare & dental benefits; smart, friendly colleagues and boss; working in a difficult environment gave me the skills to take on any challenge as I advance in my career.
Cons
I was at Medscape, a division of WebMD, for just about five years. If I had to describe middle management in one word, it would be "dysfunctional", with an alarming level of immaturity and cliquishness. One minute, I would be told to take more initiative and ownership of my work; the next, I was being micromanaged. All this coupled with constantly shifting priorities, absolutely no positive reinforcement, being underpaid, and having to document every single interaction in case my manager decided to throw me under the bus made for a VERY unhappy work environment - and this is not just my experience, as almost every single one of my teammates experienced the same. Also, forget about actually getting a promotion, even if you've been there for years - WebMD does not like to promote from within. Smart, hard-working colleagues of mine that deserved more responsibility would usually end up leaving the company for better opportunities. It's no wonder that there have been so many layoffs there, even though the job market is actually improving.