Place steaks side by side in a large casserole dish. Add orange juice, cider vinegar, and Worcestershire sauce. Marinate uncovered in the refrigerator for 45 minutes.

Preheat oven to 425°F (220°C). Remove the casserole dish from the refrigerator. Cover steaks with plastic wrap and let them come to room temperature for at least 15 minutes.

Place steaks on a clean work surface and rub generously with steak seasoning and freshly ground black pepper.

Heat olive oil in a cast-iron skillet over high heat. Sear steaks in the skillet for 2½ minutes on one side. Flip and sear the other side for 2 minutes.

Transfer the skillet with steaks to the preheated oven. Bake until steaks are firm and reddish-pink to lightly pink in the center, approximately 8 to 10 minutes. Use a thermometer to ensure an internal temperature of 130–140°F (54–60°C).