Combine Pineapple Juice (1/2 cup), Soy Sauce (2 tablespoon), Worcestershire Sauce (2 tablespoon), Red Wine Vinegar (1 tablespoon), Brown Sugar (1 tablespoon), Garlic (2 clove), Fresh Ginger (1 tablespoon), Kosher Salt (1 teaspoon) and Ground Black Pepper (1 teaspoon) in a small bowl and whisk.
Place Sirloin Steak (18 ounce) in a gallon size ziplock bag and pour marinade over steak. Squeeze out as much air as possible and seal bag. Marinate steak for 3-4 hrs in the refrigerator.
To make the Jack Glaze combine the Brown Sugar (1/4 cup), Pineapple Preserves (1/4 cup), Killer Hogs Vinegar Sauce (1/4 cup), Jack Daniels Whiskey (2 fluid ounce), Pineapple Juice (2 fluid ounce), Crushed Red Pepper Flakes (1/4 teaspoon) and Sesame Seeds (1/4 teaspoon).
Remove steak from marinade and drain excess liquid. Season both sides with Kosher Salt (1 tablespoon) and rest at room temp for 20-30 minutes
Prepare charcoal grill for direct cooking at 550 degrees F (290 degrees C).
Lightly oil cooking grate and place steak on grill. Cook for 6 minutes (twist steak half way for grill marks)
Flip the sirloin and repeat the process. Brush the top of the steak with warm Jack Glaze 2 minutes before removing from grill.
Rest the steak for 5-7 minutes before slicing to serve.