Vinaigrette:
Place vinegar in a medium bowl. Slowly whisk in the oil until emulsified. Season with salt and pepper, to taste.
Steak:
Preheat the broiler.
Broil skirt steak until cooked to desired temperature, about 5 minutes. While broiling, baste it occasionally with soy sauce. Remove from heat and let stand while you prepare the salad.
Salad:
Place lettuce in a large bowl. Drizzle with some of the vinaigrette, sprinkle with oregano, and season with salt and pepper, to taste; toss to combine. Add more dressing, if desired. Divide salad among 2 plates. Arrange tomato, onion, olives, and pepperoncini around the plate.
Slice steak into thin pieces and divide evenly among salads. Serve.
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