Pros
If you want to have creative control over how a set of applications are designed, this is a good fit. Be prepared to give and get critiqued. The development and product team have "throw your ideas on a whiteboard" design meetings generally at the end of the day once or twice a week. It provides a time to get our heads out of the weeds of day to day work and think about the future of the product we are making. It really helps us solve some of the bigger product architecture and design decisions. The product team and development team are closely knit. We all work in the same area, constantly communicate with each other, and are always open to change. The workplace has a very flat structure. If you have a question, find them and ask it, everyone. We all work together fairly well; the small company environment helps with that. The company caters to more flexible schedules, just be on time for the stand-up meeting in the mornings.
Cons
Before this last year we had some problems, and while most of them have been solved, it did cause frustration with the development team. We had communication issues between the product team and marketing. Randomization was a big issue then, as each sale had some new feature attached to it. At the time, the development and product teams brought these issues up on more than one occasion to little or no avail. As previously stated, these problems have largely been solved with the newer hires and some investor involvement. As a UX Designer, it can be a little difficult to receive customer feedback in a smaller company. We don't really get any documented information from missed sales (something the company is finally addressing) which can prolong user research times. The product team has to work with marketing and sales on the company website, marketing materials, and upkeep doesn't happen often, but can completely stop my work for a week or two. I would rather it fall on me than the rest of the team, which it does more often than not, but with a smaller company, you have to make some sacrifices. The product management team is spread a little thin and has to wear quite a few hats: quality assurance, sales training, website management, and tech support can and will fall under our purview.