Slice the steaks into 1/2-inch wide strips. Pound the strips to about half their original thickness. Place the steak in a bowl; pour the Italian dressing over the meat; allow to marinate at least 2 hours.
Mix together the cream cheese and jalapeno pepper in a bowl; set aside. Remove the strips from the marinade and lay out on a flat surface. Spread about 1 teaspoon of the cream cheese mixture on each strip.
Preheat an outdoor grill for high heat and lightly oil grate.
Remove the strips from the marinade and lay on a flat surface. Spread about 1 teaspoon of the cream cheese mixture on each strip. Fold the meat around the cream cheese mixture to form a ball. Wrap each ball with a slice of bacon. Secure bacon with water-soaked toothpicks or metal skewers.
Cook on preheated grill until steak is no longer pink, about 4 minutes per side.
