Some of my past employers were pretty good about authorizing small and medium expenditures quickly, or in some cases not requiring any authorization at all.

This feature almost always went away as the company grew and the abuse became too much to ignore. I thought it would be safe to trust developers and to deal with isolated abuse when it came up, but the number of people who see any spending perk and treat it like a target they need to maximize is way higher than I ever thought.

There are a lot of examples of this, like companies that offer to pay for dinner if people have to stay late. This seemingly always turns into a game where people hang out in the office and scroll on their phones until the allowed time arrives, then they take their dinner and leave. This doesn’t happen at small companies where you can witness what people are doing, but cross the threshold to big company and many people start doing whatever they can get away with.

There was a big story a few years ago about how employees at a big company were even caught using this perk to order their home groceries because the DoorDash like service they used had launched a section where they could get those things delivered with their food. It was crazy that employees making mid six figure salaries were still brazenly breaking the rules for personal gain of a couple hundreds of dollars per month.