Hi Chuck,
Hopefully someone with SS POS will jump in with the details. Until then, I'll share how it is done with the POS we use (LSS). I bet it's a very similar or identical process.
As part of our daily closing, the pos generates individual files with cutting instructions for each new order. (in our case, named with the ticket # 6452.wz2, 6453.wz2, etc). They're stored on a network drive which is common to the POS and Wizard systems.
From there we just open them up from the wizard machine, when ready to cut, and it knows the dimensions etc.
I'd be willing to guess both systems work the same way, but hopefully someone who has done this with Specialty will chime in.
Mike