In a large skillet over medium heat, combine the cooked ground beef, Worcestershire sauce, garlic powder, onion powder, and black pepper. Stir until heated through, about 3-4 minutes.
Remove the beef mixture from the skillet and set aside. In the same skillet, add 1 tablespoon of olive oil and heat over medium heat.
Place one tortilla in the skillet and sprinkle 1/4 cup of cheddar cheese and 1/4 cup of Monterey Jack cheese evenly over the tortilla.
Add 1/4 cup of the beef mixture, followed by a sprinkle of diced onions, tomatoes, and pickles. Top with another 1/4 cup of cheddar and Monterey Jack cheese.
Place a second tortilla on top and press down gently. Cook for 3-4 minutes until the bottom tortilla is golden brown and the cheese is melting.
Carefully flip the quesadilla using a large spatula and add the remaining tablespoon of olive oil to the skillet. Cook for another 3-4 minutes until the second side is golden brown and crispy.
Remove from the skillet and let cool for a minute before slicing into wedges. Repeat with the remaining tortillas and filling.