Upload files to wordpress site using ftp folder

I was asked by a higher up at my company if I can figure out a way to upload and possibly display files on a wordpress website by a person dropping a file into a folder on their desktop. He seemed confident that is was possible but when I asked him he said he knows it is yet he has never done it himself.

My first thought was dropbox but unfortunately the only dropbox plugins I can find don’t accomplish what I need (unless I missed one)

Is there anyway that I can accomplish this? I’m willing to get more complicated than just installing a plug in if necessary.

Thanks for any responses.