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Preheat the oven to 400F.
Toss the butternut with 1 teaspoon olive oil, ½ teaspoon kosher salt, and ⅛ teaspoon black pepper. Spread on a parchment-lined baking sheet and roast for 30 to 40 minutes, or until tender.
In a large mixing bowl, combine the kale with 1 teaspoon olive oil. Massage the oil into the kale to help tenderize it, about 3 minutes.
To make the vinaigrette, whisk the vinegar, syrup, and mustard with ½ teaspoon kosher salt and ⅛ teaspoon black pepper. While you whisk, gradually stream in remaining 3 tablespoons olive oil and whisk until incorporated.
Just before serving, cut the apple into roughly ½-inch dice.
To assemble the salad, divide the prepped kale among 4 bowls. Top with the roasted butternut, diced apple, pecans, craisins, chicken, and crumbled goat cheese.
Drizzle vinaigrette over the entire bowl, about 1 ½ tablespoons each.