Sorry to sound negative, but everyone has an undergraduate degree nowadays, and "working towards" qualifications basically means that he doesn't have them. It would be better to complete these qualifications first, then start looking for jobs.
Even if he gets those, he's still most likely going to have to start at the bottom, unless he wants to take a risk and start his own business (although it's doubtful that he has the resources, experience and skills necessary to do this if he has been working in retail for so long).
To turn it on its head, there's no point spending the money on a qualification if he can't get in the door anyway.
He's been running a store, not stacking shelves. Let's avoid the put-downs, please.