Preheat the oven to 350 degrees F.
Cut the steak into 3 1/2 to 4-ounce pieces. Pound each steak out evenly to about 25 percent of its original thickness. Season them with pepper. On top of each steak place a slice of provolone, some sage leaves, and 2 slices prosciutto. Roll them up into a pinwheel and secure with toothpicks.
Heat the oil in a skillet over medium-high heat and saute the pinwheels until they are brown on both sides. Place them in the oven and roast until they are medium rare, about 7 minutes. Let the steaks rest for 5 minutes before carving them into bite-sized wheels.
Put the skillet back on medium-high heat. Add the remaining sage leaves and cook until they are crispy. Drain them on paper towels; use them to garnish steak.