In a large mixing bowl, toss cubed butternut squash with olive oil. Sprinkle with a few generous pinches of salt and pepper, and toss until combined.
Spread the butternut squash out in an even layer on a parchment-covered baking sheet. Bake for 15 minutes, then remove from the oven and flip the squash for even cooking. Bake for an additional 10-15 minutes, or until the squash is tender and slightly browned around the edges. Remove from oven and transfer back to the large mixing bowl.
Add couscous, kale, cranberries, walnuts, goat cheese, and vinaigrette, and toss to combine.
Serve warm, or refrigerate in a sealed container for up to 3 days.
To Make The Vinagirette:
Whisk all ingredients together until combined. Taste, and season with additional salt and pepper if needed.