Does anyone know how to add a watermark to all video playout?
There is no inbuilt way to watermark the output. Why would you want to do that?
To protect all the videos being played out.
You can put an transparent layer on top of your playout.
This client has a playout and watermarking module.
Download from here.
https://casparcgforum.org/t/simple-video-playout/61
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And it does exactly the same… putting an transparent Layer on top 
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How can I add a transparent layer on the top in CasparCG?
It‘s as easy as playing any other layer. Be sure to use something with transparency (alpha channel) like a png graphic and play it on a layer with a bigger layernumber than your playout uses.
Can you show me an example?
What is the problem with playing a PNG? What client do you use?