Place steaks side by side in large casserole dish. Add orange juice, cider vinegar, and Worcestershire sauce. Refrigerate, uncovered, for 45 minutes.
Preheat the oven to 425 degrees F (220 degrees C).
Remove casserole dish from refrigerator. Cover steaks with plastic wrap and let reach room temperature, at least 15 minutes.
Heat olive oil in a cast-iron skillet over high heat.
Place steaks on a clean work surface and generously rub with steak seasoning and black pepper.
Cook steaks in the hot skillet until lightly browned on the bottom, 2 1/2 minutes. Flip and cook until browned on the other side and red in the center, about 2 minutes more. Place skillet, with steaks, into the oven.
Bake in the preheated oven until steaks are firm and reddish-pink to lightly pink in the center, 8 to 10 minutes. An instant-read thermometer inserted into the center should read from 130 degrees F (54 degrees C) to 140 degrees F (60 degrees C).
Remove steaks from oven; season with salt. Let sit for 5 minutes before serving.