Pros
People are great—many of the team members are sharp, dedicated, and want to innovate. I formed closer bonds and friendships here than any other place I've worked. HR team does a good job of trying to keep employees happy with diverse events, food, and other surprises. Office is generally a fun and laid-back environment.
Cons
Middle management ties everything in knots. Product Team (ie the team responsible for maintaining and innovating the website) is terribly disorganized, mismanaged, and over-rewarded despite minimal contributions, and two royally massive screwups (including the famed disastrous relaunch of Seamless.com). There's also blatant favoritism towards the Grubhub / Chicago side of the company. The CEO tried to run Seamless into the ground and everyone in NY was aware of it. Grubhub management put in charge ahead of Seamless' management, site restructuring with Grubhub as a priority (the main reason for the site relaunch fiasco), hiring in Chicago over NY, forcing NY people out by hiring people to be their bosses, but they're in Chicago, trying to run and position Seamless as an 'authentic new york' brand when the management isn't even in New York.