The mistake I've seen a few companies make is hiring in the wrong kind of experience (and I'm gonna use that word instead of "old" since I don't think the "old" bit is actually the issue). For example - say you want to "build a worldwide sales channel". Go find somebody who's running a worldwide sales channel and poach 'em... right? Nope. Coz running a successful worldwide sales channel is a very different process fr…
Also, I don't know, wouldn't somebody who built a sales channel (whatever that is) in the past have done so with completely outdated methods? Presumably fax machines and telephones?
1) There have been largish successful organisations built since the web was invented ;-)
2) Lots of pre-web skills skills are transferable to more modern technologies. Most of the work in creating and building sales channels - especially internationally - is understanding people relationships, legal issues, managing recruiting and scaling of organisations not code, etc.
3) There are domains where large multinational organisations are still built using telephones, personal relationships and boots on the ground. If you're looking to build the next Oracle or SAP a bunch of retweets and facebook likes are not going to help.