I have worked with him for all his 4 years there. He is a good, competent, typical startup guy who fits better at an early stage. But I think that the way he is (and many others in the valley are) measuring payout is flawed. I hope this audience doesn't generalize and extrapolate Jeff's observations. Especially in the context of Box.
For those who have never worked at Box, it's very hard to describe how special that place is. The culture is (or at least was) hands down one of the best I've experienced. The bar to entry is high, both culturally and technically. Everyone has a drive to do the right thing for the customer, and has had a meaningful opportunity to contribute. All of us there have built amazing relationships and grown (tremendously) professionally over the years. Many of us have even gone on to build successful businesses, on the strength of those relationships (e.g. http://interviewkickstart.com).
THAT is the payout.
The fact that Sutton can now hop from one good startup to another in the valley is the payout.
The fact that companies look at his resume and trust him to help their IT infra grow from 40 to 1000, is the payout.
The fact that he can proudly recount to his friends, that he worked at Box early, is the payout.
The fact that he can call upon any relationship from those years and they pickup his phone, is the payout.
The fact that he is not worried about his next startup job in the valley anymore, is the payout (that wouldn't have happened had he stayed at IBM).
The fact that he can put down payment to a house and raise a family in a decent part of Bay Area, is the payout.
And btw, the fact that his IT management helped 1000 of us serve a million+ customers to organize and secure their data, is also the payout.
In a startup, you value people and an opportunity to do meaningful things, above everything else. You want to be a part of that small group, that moves the needle in this massively morbid and unpredictable world. Anything else, is bonus.