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Make the salsa criolla: In a medium bowl, stir together the oil, vinegar, parsley, garlic, bell pepper, onion, and tomato. Season to taste with salt and black pepper. Set aside.
Make the provoleta: Position a rack in the upper third of the oven and preheat to 425°F. To a small cast iron skillet over medium-high heat, add the oil, followed by the provolone. Sprinkle half of the oregano and red pepper flakes on top. Cook, flipping once, until the cheese begins to bubble and the edges brown, 4–6 minutes total. Bake until the cheese is melted and golden brown, about 3 minutes.
Sprinkle the provoleta with the remaining oregano and red pepper flakes. Serve immediately with the salsa criolla, chimichurri, and bread.