Acrobat DC Pro and Adobe Sign

So our company is wanting to use the adobe sign in this way:

the sales rep sends to customer and they sign;

it's sent to account setup and they sign;

it's sent to the art department and they sign;

it's then sent back to the sales rep as completed.

So the questions I have are:

1. I need to have the customer be able to upload artwork while they are signing.

2.Once it is complete and is returned to the sales rep, I need the sales rep to be able take their order and add it to the documents, then send back to account set up for processing.

Is it possible to do these things?  Right now I have Acrobat DC Pro personal version, and have been told if you have a business version, that you can. The chat feature is useless so I hoped someone here could help me.