I did not guide the deli on what I needed my Prosciutto to look like so I had to improvise a little. Try to get lean slices with the fat mostly on the edges. My slices were divided by fat. In some cases I overlapped other slices to make it work.
Place the slices on a wide work surface, about 2" apart. Spread the goat cheese over the prosciutto slices.
Divide the fig quarters evening over the cheese.
Drizzle the dressing over each slice. Sprinkle pepper over each slice.
Arrange the arugula alternating the tops and stems as shown making sure some of the tops of the leaves overlap the edges of the prosciutto.
Starting on a short side roll up the slices in a tight roll.
Slice each roll in half as shown and arrange on a plate.
If you are making these ahead of time make, plate and cover them with a damp paper towel and plastic wrap. Make these a maximum of 2 hours ahead.