In a large skillet, heat the olive oil over medium heat. Add the ground beef, breaking it apart with a spatula. Season with salt, black pepper, garlic powder, and onion powder. Cook until browned and fully cooked, about 7-10 minutes. Drain excess fat if necessary.
While the beef is cooking, prepare the salad base by placing the chopped romaine lettuce in a large bowl.
Once the beef is cooked, let it cool slightly before adding it to the bowl with the lettuce.
Top the salad with cherry tomatoes, dill pickles, shredded cheddar cheese, and diced red onion.
Drizzle with Thousand Island dressing and toss gently to combine. Serve immediately.