Block

• Great perks, food, and environment in the SF office.
• The company likes to contribute to open source.
• The engineering organization is strong (but other organizations are much less strong by comparison).
• Products you care about, helping sellers grow.

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 the 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.

The company needs a sensible, sane, and realistic plan, implemented by a stable, high-functioning management team.