Heat olive oil in a skillet over medium-high heat. Season steak generously with salt, black pepper, and cayenne. Sear steaks for 5 to 6 minutes. Flip; add diced onions to the sides. Cook until steaks begin to firm and are hot and slightly pink in the center, 5 to 6 minutes more. Push onions under the steaks and cook until browned but still crunchy, 2 to 3 minutes more. Remove steaks to a plate.
Preheat the oven to 425 degrees F (220 degrees C).
Place rolls on a baking pan lined with foil. Hollow out the top of each roll by cutting in at a 45-degree angle. Pinch off some of the bread inside to make room for the filling.
Slice steaks into thin strips, then across into 1/2-inch pieces. Transfer to a mixing bowl. Add the sauteed onions and accumulated juices. Toss in pickled peppers, cream cheese, 1 1/2 cups provolone, 1 teaspoon salt, and 1/4 teaspoon pepper. Mix until thoroughly combined. Taste and season with salt as needed. Spoon filling into the rolls and top with remaining provolone cheese.
Bake in the preheated oven until cheese is melted and edges of the rolls are starting to brown, about 15 minutes.