Set a skillet over medium-high heat and wait until it’s hot, then add the ground beef in crumbles. The meat should start sizzling right away, which helps it brown instead of turning gray.
Break the beef into smaller pieces with a wooden spoon or spatula, then add the Italian seasoning, paprika, kosher salt, black pepper, garlic powder, and onion powder as it cooks for about 5 to 7 minutes. The beef is ready when you see no pink left and the edges are slightly crisped with a savory, burger-shop aroma.
While the beef cooks, stir together the mayo, onion powder, garlic powder, ketchup, maple syrup, dill relish, yellow mustard, apple cider vinegar, and salt in a small bowl or large liquid measuring cup. The sauce should look smooth and creamy, and it tastes even better after it sits for a few minutes.
Divide the chopped romaine among 4 bowls and spoon the hot cooked beef over the greens. The warm meat should lightly soften the top leaves without wilting the whole salad.
Scatter the cherry tomatoes, dill pickles, red onion, and grated cheddar cheese over each bowl, then drizzle with as much burger sauce as you like. You want every bite to have a mix of cool crunch, savory beef, and creamy tangy sauce.