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Roast the squash. Preheat your oven to 400˚F and line a baking sheet with parchment paper. Drizzle the squash with olive oil and season with salt and pepper. Roast it on the baking sheet for about 25 minutes, or until the squash is tender with golden edges.
Make the dressing. In a small bowl or mason jar, whisk the dressing ingredients (tahini, lemon juice, maple syrup, olive oil and salt & pepper) together until smooth. Set the dressing aside for later.
Massage the kale. Place the kale in a big bowl and add 1 tablespoon olive oil and a pinch of salt. Use your hands to massage the kale. This softens the kale and takes away bitterness. It can make a huge difference in the texture and flavor. Don't skip this step!
Assemble the salad. When the squash has cooled, add it to the kale along with the rest of the salad ingredients. Before serving, add the dressing and toss to evenly coat the salad.