Preheat the oven to 400? F.
Trim the stalk ends off the asparagus and drizzle with 1 teaspoon olive oil. Use your hands to make sure all the stalks are lightly coated and sprinkle the asparagus with sea salt.
Wrap 3-4 stalks of asparagus in 1 thin slice of prosciutto. Place the bundle on a baking sheet seam-side down. Repeat for the remaining asparagus and prosciutto. Bake for 15 minutes or until the asparagus and prosciutto are crispy.
Heat the balsamic vinegar in a small skillet over medium-high heat while the asparagus is roasting. Bring to a full boil and cook, stirring occasionally, until the vinegar has reduced by ? of its original volume and is thick, about 3-5 minutes. Set aside until you're ready to use.
Add the chopped pears, butter, pure maple syrup, cinnamon and salt to a small pot and heat, covered, over medium-high heat. Cook, stirring occasionally, until the pear has softened and is caramelized, about 8-10 minutes.
Transfer the prosciutto-wrapped asparagus to a serving platter. Add the spiced pears, drizzle with balsamic reduction and serve!