Preheat oven to 450° F. Lay flank steak on cutting board with grain perpendicular to you. With a very sharp knife, slice steak open like a book, leaving the one side still attached. Spread pesto evenly over the two “pages” and sprinkle bread crumbs over the pesto.
Lay the slices of cheese one inch in from the edge evenly over the filling. Roll steak up so that the grain is running the length of the roll (the direction of the grain is important, since flank steak needs to be cut against the grain). Make sure cheese is tucked inside, tie securely in several places with kitchen string. Sprinkle with salt and pepper. Heat a large skillet with an ovenproof handle until very hot. Add a small amount of olive oil and brown meat on all sides. Place in oven and bake about 18 minutes for medium doneness. Cover with foil and let stand 10 minutes before slicing on an angle into 1/2 inch slices.