Does anyone know how LinkedIn created this greyed-out help functionality?
I need to do something similar for my iPad app.

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To create the illustrations per se, you might need help from a designer. However, if you can get by with simple labels and buttons. You can create it easily in the Interface Builder.
In XCode, go to File->New File, in the User Interface part, choose View. Name it and click create.
Open the file by clicking on it in the XCode file list.
To give it that kind of background, open the Attributes Inspector (Menu View->Utilities). There, you will see
background, choose black. You will also seealpha, to give it transparency. Choose the value you like.Place labels, buttons and images as you wish. And there you are.