In an oven-safe 12-inch skillet over medium heat, cook the pancetta until crisp. Remove with a slotted spoon to a paper towel-lined plate. Add the Brussels sprouts to the empty skillet, season with salt and pepper, and cook, tossing occasionally, until they start to brown. Remove from the heat and stir in the olive oil and balsamic vinegar.
Place the skillet in the oven and cook for 15 minutes, tossing once or twice. Increase the oven temperature to 425 degrees F, stir in the pine nuts, and cook for an additional 10 minutes. Remove from the oven and stir in the pancetta and dried cranberries.