Preheat oven to 400*F.
Toss diced butternut squash with 1 tsp oil, ½ tsp salt, and 1/8 tsp pepper. Spread on a lined baking sheet and roast for 30-40 minutes or until tender.
In a large mixing bowl, combine kale with 1 tsp olive oil. Massage oil into kale for about 3 minutes (this will help tenderize the kale).
In a small bowl, whisk vinegar, syrup, mustard, ½ tsp salt, and 1/8 tsp pepper. Once incorporated, gradually whisk in 3 tbsp olive oil until well combined.
When close to serving, dice the apple into ½ inch pieces.
Assemble salad by dividing kale between 4 bowls and topping with squash, apple, pecans, craisins, chicken, and goat cheese evenly between the four bowls.
Drizzle vinaigrette over bowls evenly. Serve right away.