Automated Email to Supervisor?

Hello! I have a board for users to request and automatically receive a PDF certificate of completion for a course using DocExport. The user adds their email and the PDF is sent to them. This has worked really well but I had a request to have this file also sent to the person’s supervisor automatically as well. So, they would not include the supervisors email, it would be based on the facility the user stated was their worksite. I have columns for the worksite name, as well as a column that includes the generated PDF. Is it possible to set up an automation in which if a person states they work at a specific site the generated PDF would be sent to a specific email address? Each supervisor is not a user of guest on the board.
Thank you for any advice you can provide!