Preheat the oven to 375 degrees . In a large skillet, heat 3 tablespoons olive oil over medium-high heat until rippling. Season the beef with salt and pepper, increase the heat to high and cook in the skillet for 3 minutes; flip and cook for 2 minutes more. Transfer to a bowl.
In the same skillet, heat the remaining 1/4 cup olive oil over medium heat. Add the peppers and onions, season with salt and pepper and cook over medium high heat, stirring, until softened, about 8 minutes.
Place the roll bottoms on a large rimmed baking sheet and top each with the beef and vegetables; sprinkle with the cheese. Bake until the cheese is melted, about 6 minutes. Transfer to a platter and cover with the roll tops.