Pros
CEO seems like an awesome leader even if he is completely disconnected from the reality of how management is treating hourly employees. For the most part, the benefits are Great! High pay at every position but you will pay a price for this. Cash App advertises unlimited paid time off which was changed to a "flexible" Paid Time Off policy requiring manager approval. This often results in no Paid Time Off.
Cons
I can't speak for Square Inc as a whole, though its Cash App business is hamstrung by exploitive practices, incompetent managers, and inconsistent policies. For example, you may be asked to do a task without training, then when you ask questions, they act as if they had trained you. This is frustrating and makes for a terrible experience. Upper management throws money at HR issues rather than working to understand the challenges to make meaningful change. Often senior management resorts to firing multiple staff who violate policies without adequate training. To make matters worse policies change weekly with little to no notice. Turn over is very high and their solution is mass hiring to replace those they cut. Management pats themselves on the back for hiring diversity. The truth is there is no one of color in upper management positions. To make matters worse they don't check references or perform due diligence in their hiring. All that's required is a minimum required background check.