-People are added to the middle pretty consistently. That is, it's becoming more and more likely to see your role effectively demoted because they decide to add a level of management between you and your boss, or boss's boss, etc.
-Decisions are now mostly by committee. In Square's earlier history, decisions were generally made quickly by informed leaders. Today, processes are much, much slower and the company is becoming less nimble.
-Burned by the IPO. Many employees at Square, especially members of our Finance Team, took substantial pay cuts to work for Square -- sometimes in excess of 50% -- under the promise that there would be a big IPO someday and we'd make up that loss in stock. However, with the substantial cut in Square's valuation, many employees have stock option grants that are entirely in the red. To make up for these losses, the company issued one time RSU grants to older employees who might have been burned. My RSU grant was the equivalent of a 7.5% salary bonus, which takes a year to vest and will be taxed as income.
-The transparency that Square used to treasure is disappearing. It used to be that there was no product or financial plan that wasn't shared among employees. Today, a combination of unplanned leaks to the press and the demands of being a public company have ended a lot of that transparency.
-Out of touch leadership. Jack is a very inspiring leader and has an excellent understanding of design and usability. However, his conviction of being a visionary contradicts current market forces.
-Lack of career mobility. Square is very proud of its "go/grow" and "go/careers" programs which purportedly allow employees to find new roles at the company if they feel they're not developing in their career. However, very few employees are promoted at Square, particularly on the Finance and Business teams.
-Apparently Square is perfect? It's very rare for Square to admit something didn't go well or it made a mistake. The policy seems to be to just let the problem disappear and hope nobody asks about it. Products are often launched and then shifted permanently to the back burner. Metrics post-launch are rarely checked and very few financial resources are oriented towards product launches.
-Dead weight remains. People who are under-performing or are becoming caustic to the organization are very, very rarely fired and only occasionally mitigated. On the few occasions someone is fired or mitigated, of the person who replaces them is just as bad, they let that person stay in role indefinitely rather than embarrass themselves twice and have to hire for the role a third time.
