Pros
I love working for Square, the company. The work I do goes directly to our customers and helps them build their business. When I see or meet Square sellers out in the world, I'm motivated and inspired to continue the work I do at Square. Additionally, Jack's leadership is inspiring. I trust him to have clear intention for the business, but also care what's happening inside the company. I feel like I can approach him and question how decisions were made, or why we do things the way we do.
Cons
The sub-levels of leadership are awful. Some orgs are run with no care for the employees, but rather driven by data. Some orgs are managed haphazardly, and with no transparency whatsoever. Managers are leading groups of people, without knowledge or understanding of the work they ask their employees to do on a day-to-day basis. This has led to zero trust and high levels of frustration. How can one be considered successful in the eyes of a manager with no context for success? My boss only "knows" I'm doing well when he hears it from others, but does not seek it out, nor give me the benefit of the doubt when approached with feedback.