Pros
Everyone has a sense of ownership and is empowered to do what they need to do. Lots of room to change roles, move around, wear as many hats as you want. The stock will almost certainly be worth something. The company has a real purpose and is generally useful/applicable/liked by real people (unlike a lot of other companies you could be working for). Getting time off is as easy as chatting with your manager - typically no questions asked. The food program is amazing with very high-quality comped breakfast/lunch/dinner. Rapid growth translates to continuous learning opportunities and a work environment that never gets boring. As an engineer - the learning opportunities never end!
Cons
Any "cons" need to be prefaced with this: remember that Square is an extremely rapidly growing company that feels like a whole new workplace every 6 months. I've tried to only list the more consistent or recurring cons here, but all of them are consistently trending positively (or I wouldn't be working here anymore, really!). Any of these cons could be gone in a month or two, or replaced with new ones. There's just no way to know! That said: - Immature leadership has been an ongoing theme for my entire tenure. It's been a problem at every level of leadership from executive on down at some point or another. On the other hand - I think this is to be expected of a company this age and size, and is usually course-corrected eventually. - Immature HR (incl. compensation adjustment and talent review). First iterations of talent review were downright insulting: we were rated by shape (circle, square, or star) like kindergardeners. Luckily we acknowledged that was a horrible idea and have never done it again - but our cadence of performance feedback has remained random at best. Same goes for cadence of compensation adjustment. If you get a job here - NEGOTIATE UP FRONT - there's no telling how many months or years it might be until someone thinks to themselves "oh maybe we should look at comp again!". Note: this situation has already improved immensely with the introduction of a consistent engineering ranking/ladder system - if we manage to keep it more than a year, that is. - Rampant politics and personal agendas. To be expected at any growing company. We have them too. Nothing special to see here, move along. - Oncall policies. No overtime pay for brutalizing oncall shifts are the norm. No compensation for personal phone use either. Occasionally you'll get a "thank you" from someone. - Not enough bathrooms. Not kidding. Try and find a free stall or urinal sometime after lunch. Good luck!