Pros
- Great perks, food and environment in the SF office. - Company likes to contribute to open source. - Engineering org is strong (but other orgs are much less strong by comparison). - Products you care about, helping sellers grow.
Kontras
- Intensely political environment. - Constant re-orgs and management changes, like every month, to the point of being an internal joke. - Scandal central. Every high level manager sleeping with every other high level manager's girlfriend. - Company is run by high functioning alcoholics. You will be expected to DRINK. - Company has wasted hundreds of man years of effort (see Square Wallet, Pay by Name, Square Order, etc.) and now lacks direction. - Payments space is a race to the bottom, competition from PayPal, Amazon etc. is fierce. - Sky-high valuation is not justified by company's fundamentals. - Tech stack is disliked by many engineers and is burdened by years of tech debt mostly accumulated during the Starbucks launch. - High attrition, especially in the remote offices, and very especially in New York (>30%/yr). p.s. most of the glowing reviews here were written by HR