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Place 5 chopped bacon slices in a large skillet and cook over medium heat until browned and crisp, about 12 minutes. Turn off the heat.
Use a slotted spoon to transfer the bacon to a paper towel-lined plate. Transfer 1 tablespoon of the rendered bacon fat to a large bowl and discard the remaining fat.
Whisk ½ cup ranch dressing, 1 finely chopped canned chipotle chile in adobo sauce, 3 tablespoons brining liquid from pickled jalapeños, ½ teaspoon kosher salt, and ½ teaspoon black pepper into the bacon fat until combined.
Stir in 1 pound chopped broccoli florets, 1 diced small red bell pepper, ½ finely chopped medium red onion, 1 tablespoon coarsely chopped pickled jalapeño slices, 3 ounces shredded sharp cheddar cheese, and half of the bacon.
Garnish with the remaining bacon and more pickled jalapeño slices, and serve at room temperature or chilled.