There is a existing Enhancement request for this functionality to be added: https://blackbaudk12.ideas.aha.io/ideas/K12OR-I-46​.

In the interim you can use this option(provided in the Enhancement Request URL above): add the signature to the footer of the transcript using the <img src= > html tag. You could upload an image of the signature to the Misc uploads section in on Message and then use the <img src> tag to display it. one downside to this is that if you need to be sure who has access to run official transcripts because anyone that has access to run this transcript will be able to produce it with the Dean's signature. You could always delete the signature after you are finished running them so it wouldn't be there all the time. It is not ideal, but it would keep from having to signing all the transcripts individually. I have been using adobe to digitally sign mine. I have to do them individually in adobe, but I like to put eyes on all of them before they are submitted, so I don't mind signing each one because it ensures that I have to look at it.