I would say be careful about having someone make the design for you. My daughter took a design to a person who turned the design into a digitized embroidery design. He embroidered the design onto 2 bags and then refused to give my daughter the digitized design. There are other details to this story but, this is the bottom line to the story.
I can't guide you on software since I don't use that part of my machine. There are a lot of free embroidery designs on the web as well as to purchase. My favorite site is Embroidery Library.
http://www.emblibrary.com/