Preheat oven to 400 degrees Fahrenheit (200 degrees Celsius).
Toss cubed butternut squash with 2 tablespoons olive oil, salt, and pepper on a parchment-lined baking sheet.
Roast squash for 20-25 minutes or until tender and lightly browned, then allow to cool to room temperature.
Whisk balsamic vinegar, maple syrup, Dijon mustard, and 0.33 cup extra virgin olive oil in a small bowl until emulsified.
Place sliced kale in a large mixing bowl and massage with one tablespoon of the dressing for 2 minutes until leaves are softened and dark green.
Add the cooled roasted squash, pomegranate seeds, and toasted pecans to the kale.
Drizzle the remaining dressing over the salad and toss thoroughly to combine.
Top with crumbled goat cheese immediately before serving.