I don't know if any one factor is going to convince the brass that Perl is a winner. In my case, we started out working with MS ASP on an NT/IIS server. Every time we wanted to do anything new, we'd realize that ASP just didn't cut it, and so early on we started to switch to Perl. Now it's pretty much all we use. The "ASP guy" had to go find somewhere else to occupy his time ;)

-Guv