Yeah, at a big enterprise the larger challenge ahead of even payment is the legal arrangements. They typically sign some "master license" agreement with an aggregator like CDW. Those places don't seem well set up for software redistribution though. Setting up a Steam or AppStore clone for various utility-ware would go a long way to enabling people to access the software an enterprise doesn't mind paying for if the legal and financial stuff wasn't applying friction.

There are already software licensing providers such as 10Duke that do exactly that. Pretty much all of the licensing related problems mentioned here would either disappear or at the very least get dramatically simpler if more companies used 10Duke Enterprise as their licensing solution to issue and manage licenses. There is a better way, but sadly most businesses overlook licensing.

(the company I work for uses them, our licensing used to be a mess similar to what's described here)