Pros
What GrubHub does is fascinating. It's hard not to take extreme pride in helping restaurants get more business and make it easier for people to find and order food. No matter where you worked, you can very easily observe how your work contributed to the end product. A lot of the people, in all parts of the organization, are extremely enthusiastic and are constantly looking for ways to improve how they can contribute more. On top of that, there are tons of areas that you can work in regardless of your interest on both the technology and business operations side of things. Upon wrapping up one project, it wasn't uncommon to join another project to support another area.
Cons
Joining the company, all facets of the organization were in transition, from dealing with leadership change as a result of the merger, expanding into new business operations, and just overall headcount growth. Even though, functionally, the different areas of product development were always siloed, the camaraderie of "we're in this together" slowly faded away. The general interactions between teams became more adversarial, as if one was truly more important than the other. Rather than celebrating achievements together, it became an arms race in who can tout their goals more loudly than the other. Attitudes shifted as well as people started name-dropping members of upper management as a baseless leverage tactic. It was getting increasingly irritating to call these bluffs. Shortly after my departure, people at GrubHub now are, indeed, literally afraid of being on the wrong side of certain managers now. That's not a very great way to keep people motivated. On top of that, there was increasingly more "don't tell anyone else but..." as if this were going to make people feel better about themselves. It doesn't. The opacity in organizational and technological goals is pitch black. There have been many organizational pivots and they have all happened swiftly.