Preheat oven to 325 degrees. Toss the squash with the olive oil, salt and pepper and spread out on a baking sheet in a single layer. Roast for approximately 20 minutes or until tender. Set aside to cool.
In the bowl of a small food processor, add the cranberry sauce, mustard, yogurt, shallots, vinegar, and olive oil. Process until smooth. Season with salt and pepper to taste. Set aside.
In a small bowl, gently toss the avocado and apple with the lemon juice.
In a large bowl, toss together the kale and brussel spouts. Add the squash, avocado, apple, pomegranate seeds, pecans and dressing and lightly toss to combine. Wrap tightly with plastic wrap or transfer to an airtight container to store in the refrigerator for at least 1 hour. Can be made up to 1 day in advance.