Don't sell IronRuby, sell Ruby itself. It's not hard to find sample code (or just refactor some existing C# code) where the ruby version is quarter the size, and twice as readable than the C# version.
If you can convince people of the benefits of ruby, and then go "and now here's the party trick, you can integrate IronRuby with all your existing C# code for no effort" then I've found that works. There are also a couple of areas where ruby really shines 1) Exploration. Irb is already pretty good at this, but a REALLY killer feature would be integrated IronRuby in visual studio's immediate window under the debugger. 2) Testing. Unfortunately this is harder to sell as if you're testing other .NET code you really need the visual studio integration :-(
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