Allowing the meat to rest for 10 minutes lets the juices redistribute throughout the steak for richer flavor.
1 1/2 pounds flank steak, trimmed
1 tablespoon chopped fresh rosemary
1/2 teaspoon freshly ground black pepper
1/4 teaspoon kosher salt
1 teaspoon olive oil
2 tablespoons finely chopped shallots
2 tablespoons tomato paste
1/2 cup less-sodium beef broth
2 teaspoons brown sugar
1 tablespoon bourbon
2 teaspoons balsamic vinegar
1/8 teaspoon salt
How to Make It
Prepare grill to medium-high.
Sprinkle steak with rosemary, pepper, and kosher salt. Place steak on grill rack coated with cooking spray; grill 7 minutes on each side or until desired degree of doneness. Remove from grill; let stand 10 minutes. Cover and keep warm.
While steak rests, heat oil in a small saucepan over medium-high heat. Add shallots; sauté 1 minute. Add tomato paste; cook 1 minute. Stir in broth and sugar. Bring to a boil; cook 3 minutes or until thickened. Remove from heat; stir in bourbon, vinegar, and 1/8 teaspoon salt. Cut steak diagonally across grain into thin slices. Serve with sauce.