A bulk of letters for one recipient

@linnaroa Could you define out the question further?  Are you looking to re-use this Bulk Send process at a later time or would this be a one tine send?  Are you trying to send this one Recipient multiple envelope or just a single envelope?  Typically Bulk Send would be used to send a document to intended Recipients to take an action, such as a non-disclosure document. If you had 50 employees who needed to individually take action and then you wanted the Legal dept to get a copy, you would create a Template or Envelope that had the Legal dept set as Recipient #2 with “Receives a Copy” and Recipient #1 would be where the Bulk Send CSV would be used to specify the employee who needed to sign the document, therefore you would be sending 50 envelopes, each envelope with a unique Recipient #1 but the same Recipient #2.

I am sending 20 engagement letters under different entities to the same recipient to sign and date each letter. I was hoping to add the signature box and date at the same time instead of one by one. 

Thank David! I appreciate your time and help! I will try this with the Bulk Send feature.