The company in question uses DocuSign, and most of their clients do as well. They are big, serious companies. However, nobody is able to set up DocuSign in a reasonable way for a multi-client contract. Every company needs to use their own DocuSign.
Now, DocuSign embeds a cryptographic signature in the signed PDF. This means you can't sign a PDF twice.
So what my friend does is create the PDF to be signed, send it to one company for signatures, get it back and run it through Microsoft Print to PDF. This friendly utility happily strips away all cryptographic signatures, but importantly leaves the "signature picture" in place. And then they can send this PDF to the next company.
I joked that every time they do this, a cryptographer somewhere stubs their pinky toe on a corner.