Keep in mind that Zappos is based in Las Vegas, and that the vast majority of their employees are support staff likely making under $30K a year. If $2K is almost as much as you make in a month you might consider taking the payout and finding a new job if you're not happy with the culture.

I feel like people making only $30K a year, aren't the type of people to just jump ship because the "culture" has changed. They generally want to keep scraping by.

You're mixing up the buyout option that is a result of the switch to holocracy and the 2k option to quit you get when you first start.

This is also important to remember; most customer service organizations exemplify micro-management, with a whole layer of people who make it their job to prevent the reps from helping customers by gaming useless metrics.

Having a flat customer service organization (and valuing making customers happy) sounds like a great way to filter for reps who can think independently and find ways to make customers happy (and themselves more efficient).

$2000 to quit a job you just started seems pretty good though. You should still have your job search apparatus ready and could hopefully get another company quite quickly.

I'm actually surprised they don't see more people gaming the system, applying to get the bonus without any intention of working at Zappos.

I was looking it up how many months with 2000$ that stipend would be. Turns out it would be a single payment. Also I don't know if there come any strings attached.