Go there for a couple of years.  Have a kickass personality and be the hardest working skier at camp.  Stay later than everyone else and hike.  Get to know all of the coaches + diggers + owner.  Ask for a job.  Having comp wins under your belt helps as well as having PSIA and first aid certification.
Are you sure you want to be a digger?  I'm not sure what the situation is at Windells, but at most camps a diggers life is fucking hard.  Usually no money, always working their asses off, sometimes no free food, sometimes sleeping on the floor.  Would you be willing to do that?