In a small bowl, combine mayonnaise, ketchup, pickle juice, mustard, Worcestershire sauce, and salt and pepper to taste. Set aside.

In a large skillet over medium-high heat, cook ground beef until browned and cooked through, about 6 to 8 minutes. Drain well.

Wipe out the skillet, coat with nonstick spray, and heat over medium heat. Working with 1 tortilla at a time, add to skillet.

Top half the tortilla with ? cup cheese and ? of the cooked beef. Top with pickle slices, if using.

Sprinkle the top half with ? cup cheese. Fold in half and cook until cheese is melted and the tortilla is golden brown on one side, about 2 minutes.

Flip the quesadilla and continue cooking until all the cheese is melted and the second side is golden brown. Transfer to a plate and cover to keep warm. Repeat with remaining tortillas, cheese, beef, and pickles.

Cut each quesadilla in half and stack 2 halves on each of the 4 plates.

To serve, add one wedge of Iceberg to each plate and top with shallots and tomatoes. Drizzle the quesadillas and salad with sauce, serving more sauce on the side if desired.