I'm thinking along the lines of an arbor press. You could have a die set made that the ram of the press actuates that does several at a time.
If you already have an arbor press, the capital cost would be the die set. If you don't have an arbor press, they're terribly handy, and this would be a great reason to go to your boss with when selling him on the idea.
I just get the impression that this application is in a smaller shop and not in a big production floor given that hollow chisels and a hammer are your current production method, so I figure if you can swing a very useful piece of equipment out of the deal along with solving your problem, that's a good thing
Arbor presses really are terribly useful in a small, limited run type of shop. Press-in inserts come immediately to mind... Bearings... Spiral pins... thumbs...
The list goes on.