Preheat Oven and Prep Baking Sheet: Preheat oven to 425°F and line baking sheet with parchment paper.

Cook Bacon: Lay bacon strips atop prepared baking sheet in a single layer. Bake bacon in preheated oven until crispy, about 15 to 20 minutes depending on thickness of bacon. (Alternatively, bacon can be cooked on stovetop over medium heat and drained of excess grease on paper towel-lined plate.)

Cook Ground Beef: While bacon cooks, to a large skillet over medium-high heat, add ground beef and cook until browned and no longer pink, about 8 to 10 minutes, breaking up meat while it cooks. Once cooked, remove skillet from burner, then stir in salt and pepper. Do not drain grease from skillet.

Prepare Salad: Once bacon has cooked, remove baking sheet from oven, allow bacon to cool slightly, then crumble bacon into a large mixing bowl. To bowl, add cooked ground beef, romaine, shredded cheddar, and chopped pickles.

Prepare Dressing and Add to Salad: In a high-speed blender or food processor, blend dressing ingredients until smooth. Pour dressing over salad and stir until all ingredients are incorporated.

Chill Salad Then Serve: Transfer salad to refrigerator to chill for at least 1 hour. Serve chilled.