Slice acorn squash in half and remove the seeds. Slice into 1/2-inch slices and lay on a baking sheet lined with parchment paper. Drizzle with 1 tablespoon. olive oil and season with sea salt and ground cinnamon. Roast squash for 35-40 minutes, until tender. Remove and set aside. No need to remove the skin.
Massage the kale with your fingers with 1/2 tablespoon. olive oil for 2-3 minutes until evenly coated and tender.
To make the dressing, whisk together the olive oil, apple cider vinegar, grapefruit juice, dijon mustard, pure maple syrup, and sea salt, then add to the kale and toss well.
To assemble the salad, top the kale with squash and sliced almonds and serve.