Pre-heat the oven to 400 degrees. Line two baking sheets with parchment.
Place the cauliflower florets on one of the prepared baking sheets. Drizzle with 1 tablespoon of olive oil and season generously with salt and pepper. Toss to combine, then spread the cauliflower in an even layer, leaving a little bit of space between each floret. (This will help them get beautifully caramelized and crispy.) Briefly set aside.
Add the butternut squash cubes to the remaining prepared baking sheet. Drizzle with 1 tablespoon olive oil, sprinkle with the cinnamon and a good pinch of salt, and toss to combine. Spread the squash in an even layer, again, leaving a little bit of space between each cube.
Transfer the cauliflower and butternut squash to the oven and roast for 30 minutes, or until both are tender and lightly browned in spots. Stir the squash once halfway through the cooking time. (The cauliflower will caramelize better left undisturbed.) Let cool slightly.
Meanwhile, prepare the kale. Place the kale in a large mixing bowl and drizzle with the remaining 2 tablespoons of olive oil and the lemon juice. Season with a good pinch of salt, then give the kale a little massage. Literally rub the leaves between your fingers, massaging the oil and salt into the leaves, until the kale darkens slightly in color and becomes tender. (This will take 1-2 minutes.) Set aside.
Next, toast the pepitas. Heat a small skillet over medium heat. When hot, add the pepitas to the pan and cook, shaking the pan regularly, until they are very lightly browned (about 1-2 minutes). Transfer to a bowl and set aside.
Time to make the dressing. Whisk the tahini and ¼ cup water until very smooth, then whisk in the lemon juice, tamari, and maple syrup. If necessary, add water, 1 teaspoon at a time, until the dressing is thin enough to drizzle. Taste and season with a little salt or extra maple syrup if needed.
Add the roasted cauliflower and butternut squash, toasted pepitas, and pomegranate arils to the bowl with the massaged kale. Toss to combine. Serve drizzled with the desired amount of tahini dressing. (I recommend drizzling the salad with half the dressing, and then allowing individuals to dress their servings as they like.)