Pat steak dry with paper towels and trim visible fat. Use meat mallet to gently tenderize if desired.
Whisk together olive oil, soy sauce, red wine vinegar, Worcestershire sauce, brown sugar, minced garlic, red pepper flakes, steak seasoning, and smoked paprika until well combined.
Place steak in gallon-sized zip-lock bag and pour marinade over it. Seal and refrigerate for 4-24 hours, flipping occasionally.
Remove steak from refrigerator 30-60 minutes before cooking to bring to room temperature.
Preheat grill to high heat and oil the grates.
Remove steak from marinade, letting excess drip off, and place on hot grill.
Cook for 5 minutes per side for medium-rare (130-135°F internal temperature).
Transfer to cutting board and tent with foil. Let rest for 10 minutes.
Slice thinly against the grain and serve immediately.