Pros
Grubhub is a Chicago darling and looks great on paper (successful "start up" in Chicago, great for food and restaurant lovers, still relatively small so gives you the illusion of ownership and empowerment). There are some genuinely great employees at Grubhub -- smart with a sense of humor. The culture of the day-to-day folks is really fun and young (play board games during lunch, spontaneously nerf gun wars, etc). Office is recently renovated and beautiful; rooftop access is especially lovely in the summer months.
Cons
Leadership is immature at best and the level of politics for a company of this size is appalling. The CEO is absent, they are on their 5th CTO in 5 years (huge red flag for any company in the tech industry), and the heads of product, marketing, ops, and HR are all relatively new. In essence, you have 5 C-suite people vying for power/territory and trying to make a mark which translates to constantly changing priorities and firefighting. For product specifically, product managers are expected to just execute and be scrum masters/project managers; defining and envisioning product strategy is not valued. Finally, there is weak alignment between product managers and development teams which results in no product ownership and no accountability for timelines. Bottom line: this is not the place for product excellence nor a place to grow and learn as a product manager.