In a medium bowl, combine the finely chopped parsley, minced garlic, and oregano. Add the extra virgin olive oil, red wine vinegar, red pepper flakes, salt, and black pepper. Stir well until fully blended. Taste and adjust seasoning as needed. Set aside at room temperature for at least 10 minutes.

Remove the steaks from the refrigerator 30 to 45 minutes before cooking to bring them to room temperature. Pat both steaks completely dry with paper towels. Season generously on both sides with salt and freshly ground black pepper, pressing the seasoning firmly into the surface.

Place a cast-iron skillet or heavy grill pan over high heat. Let it heat undisturbed for 3 to 5 minutes until very hot. Add the 2 tablespoons of olive oil and swirl to coat. The oil should shimmer immediately. If it smokes heavily, reduce the heat slightly before adding the steaks.

Carefully lay the steaks in the pan without moving them. Sear for 3 to 4 minutes on the first side until a deep golden-brown crust forms. The steak will release naturally from the pan when ready. Flip once and cook the second side for another 3 to 4 minutes for medium-rare. For steaks needing more time, finish in a 400 degree F oven for 3 to 5 minutes after searing rather than continuing on the stovetop.

Transfer the steaks to a cutting board and tent loosely with foil. Rest for 5 to 10 minutes before slicing. Do not skip this step or the juices will run out when you cut.

Slice against the grain into roughly 1/4-inch thick pieces. Arrange on a serving plate and spoon a generous amount of chimichurri sauce directly over the sliced steak. Serve immediately with extra sauce on the side.