Preheat the oven to 425 F. Prick the sweet potatoes all over with a fork. Bake directly on the rack until tender, about 50-60 minutes. Allow 10-15 minutes to cool before handling.
Cut the sweet potatoes in half and scrape out flesh from the peel, leaving ¼- ½ thick peel. Brush skins with olive oil and bake for 5-10 minutes or until crispy.
Mix sweet potato fillings with maple syrup, smoked paprika, kosher salt, and cracked black pepper. Fill sweet potato filling back into the skins evenly and top with shredded cheddar cheese. Bake for an additional five minutes or until the cheese is melty.
Prepare Maple Bourbon Bacon Chopped Kit and top potato skins evenly with salad before serving.