Cook the Ground Beef: In a skillet, heat olive oil over medium heat. Add the ground beef, breaking it apart with a spoon, and cook until browned and cooked through. Season with salt and pepper to taste. Set aside to cool slightly.
Prepare the Dressing: In a small bowl, whisk together the Greek yogurt, light mayonnaise, yellow mustard, ketchup, white vinegar, garlic powder, salt, and pepper until well combined. Adjust seasoning to taste. Set aside.
Assemble the Salad: In a large salad bowl, combine the chopped lettuce, cherry tomatoes, red onion, dill pickles, and shredded cheddar cheese. Toss gently to combine.
Add the Cooked Ground Beef: Once the ground beef has cooled slightly, add it to the salad bowl. Toss everything together until the beef is evenly distributed throughout the salad.
Dress the Salad: Drizzle the prepared dressing over the salad and toss until everything is coated evenly.
Serve: Divide the cheeseburger salad among plates or bowls. You can top each serving with additional diced avocado or sliced jalapenos if desired.