Ashful
Minister of Fire
I got a portion of my BSEE paid for in this way... started working in a low-level engineering role, while they payed for me to take courses at night. It can be done, in theory... but takes damn near forever, while taking up your only time away from work, and leaving zero time for family. Maybe some companies offer a better deal, or time off to do homework, but none I've ever found. I eventually found I had to stop working and go back to school full-time, if I wanted to finish my degree in any reasonable amount of time....the best route would be to find a job in his field with opportunity for advancement where his desire for a Masters would be appreciated and maybe even accomodated somewhat. There are places that will help with tuition, or let you work from home one day a week to allow you to take night courses or save commute time so you can do correspondence work.
I suspect statistics support what I found, but I've never looked into it. I can say I've known dozens of people who have tried to do the part time / evening school thing, while working full time. Most give up after after several years, with very little accomplished. In fact, in my memory, I cannot recall a single one who completed their degree, without biting the bullet and going back full-time at some point.