To make the dressing add the water, tahini, cranberries, agave, vinegar, and salt to a blender and blend until smooth and creamy. Add more water if desired to reach your preferred consistency.
To make the salad preheat the oven to 400°. Line a large baking sheet with parchment paper. Add the squash to the prepared baking sheet and drizzle 1 tablespoon of oil on the squash, toss to coat the squash with the oil and season with salt and pepper, if desired. Bake in the oven for 25 minutes, flipping once halfway through. It is done when fork tender. Remove from the oven and set aside to cool.
While the squash is baking heat the remaining oil in a large skillet. Add the brussels and spread into one layer, let sit in the hot pan for about 3 minutes, toss and let sit again for about 3 minutes. Season with salt and pepper if desired, the goal is to char some of the brussels and make them slightly softer but not make them soft and mushy. Once you have achieved char marks on various pieces, remove from the heat to cook.
Add the kale to a large bowl with ¼ cup of dressing, massage the dressing into the kale just enough so that all of the pieces have been slightly massaged to make the kale more desirable to chew. Add the beets, apples or pears, butternut squash, and brussels. Toss all of the everything to combine.
Drizzle the salad with a little more dressing and top with pistachio bits, pomegranate arils, and croutons, if using. Serve the extra dressing on the side.