There may be a way to do it automatically in your software but it can also be done manually. I haven't done this in about 4 years since we have a versacamm but I wrote up some instructions outlining our procedure back then for someone who wanted to print with a Gerber edge and cut with a Roland cutter. Here is the step by step:
1. Design graphic for printing as you normally would. Before printing add 3 registration marks (black 1mm solid circles), in the lower left and right corners and the upper left corner. They obviously need to fit within your plotters cutting range. It's also easier if you use easy to remember spacing between the circles, like even inches, because you will have to enter that info in cut studio in step #7 below.
2. Print design with reg. marks. (in your case send file to printer)
3. Delete everything EXCEPT the desired cut line and the reg. marks.
4. Export as an .eps
5. Open Roland Cutstudio and import the .eps file.
6. Click "file", "print & cut", "file", "printing setup"
7. Click the "setup printer" icon and put in the size of the piece of vinyl you will be cutting.
7. Adjust the crop mark location in "printing setup" so that it matches where you located the crop marks. Note that there are some limitations as to how far apart you can put the marks so it's best to test your locations before you actually print the design.
8. When you click "okay" and return to the main Cutstudio page you should see 3 grey circle which represent the crop marks. These should line up with the blue cut lines, from the .eps, for the reg. marks. Note...it's not necessary to cut the circles. You can delete the cut lines for them if you choose but we usually don't bother.
9. Now you can load the vinyl in the plotter, oriented as it is in Cutstudio. Once you have it loaded move the optical sensor area of the head so that it is in line with and slightly to the left of the lower left registration mark. Do Not set the origin!
10. In Cutstudio select "Cutting" (top menu bar) and then "OK"
11. Plotter will find the lower left, lower right, and then the upper left registration marks. Once it has found all 3 marks it will begin cutting.