I know sony vegas and camtasia studio can do this. It is called "cookie cutter" in sony vegas and "callouts" in camtasia studio.
Here's a page with some tutorals
http://www.wonderhowto.com/how-to-fa...alcut-express/
and how to do it in sony vegas
http://www.wonderhowto.com/how-to/vi...-vegas-166668/