Pros
Square is very perk-oriented. The company has a great energy about it, with leaders always sporting positive attitudes. It is a very casual environment where employees can relax (until they begin work).
Cons
The positive attitude didn't have much (if any) substance behind it, and that especially goes for Support. The brunt of the company's changes were placed on the Support team, with very little information or assistance in even the biggest company changes. It is very much a chained-to-your-desk environment, where even a longer trip to the restroom is heavily questioned. Unlimited PTO becomes less of a perk and more of an onus when leaders speak critically toward employees wanting a vacation. Things move very quickly there, and not always in a good way. The Support team is expected to balance dozens of products with hundreds of features and is pulled in conflicting directions: keep someone on the phone while you investigate a messy issue, but don't let your call run long; we don't have a script, but we do have a very strict template of what you should be saying. Support employees have very little control over their situations, their days, and their growth within the company. Arguably the worst part was that it was not like this at the beginning of my time at the company, but the leadership placed an emphasis only on quantifiable data rather than on our customers — a bad sign for a company claiming to be all about its users. This is a company I had expected to stay with for a number of years, but I left as soon as I saw the direction it was heading.