Insert a PDF document to a PDF file at bookmark javascript?

I have a PDF file with several bookmarks.
I want each bookmark, when clicked to run Javascript that prompts the user to select a file, weather it be a PDF file or word file. Once the file is selected, it inserts the file into the existing PDF document at the bookmark.
Can anyone give me some advice or code to make this happen?
Greatly appreciated!

Maybe it will help you to understand if I describe what I am trying to do.
I need to create a template for a department at work.
They receive several documents and need to basically merge them into one PDF file in a certain order. For example, Contract, Pay Plan, Signature
The order changes depending on the type of customer, which is why a template that prompts to insert a PDF file (not an attachment) into the template at the bookmarks makes sense to me. This would make it so there would be no errors in the process and the people doing this work wouldn't have to remember what order for each type of customer.

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