In a medium bowl, season the ground beef with salt, black pepper, and garlic powder. Mix gently to combine.
Heat a large skillet over medium-high heat. Add the beef and cook until browned and fully cooked through (approximately 7-9 minutes), breaking it into crumbles with a spatula.
While the beef is cooking, prepare the special sauce by whisking together the mayonnaise, mustard, ketchup, pickle brine, and smoked paprika in a small ramekin.
Divide the chopped romaine lettuce evenly among four large serving bowls.
Top the lettuce in each bowl with equal portions of the cooked ground beef, cherry tomatoes, red onion, and dill pickles.
Sprinkle shredded cheddar cheese over the warm beef to allow slight melting.
Drizzle the prepared sauce over each bowl and serve immediately.