Preheat oven to 425°F (220°C). On a baking sheet, toss butternut squash with 1 tbsp olive oil, 1 tbsp honey, 1/2 tsp cinnamon, salt, and pepper. Roast for 25-30 minutes until tender.
Line a separate baking sheet with parchment. Add pepitas, 1 tbsp olive oil, 1 tbsp honey, 1/2 tsp cinnamon, cayenne, and salt. Bake for 8-10 minutes until toasted.
In a large salad bowl, combine shredded kale, shredded brussels sprouts, and pomegranate arils.
For the vinaigrette: Heat 1 tbsp olive oil in a skillet over medium heat. Add shallots and sage, cook until fragrant. Cool slightly. Whisk in pomegranate juice, balsamic vinegar, and honey. Season with salt, pepper, and red pepper flakes.
Pour vinaigrette over the salad and toss to combine. Add roasted squash, tossing gently.
Top the salad with toasted pepitas, fresh figs (if using). Enjoy your vibrant fall harvest salad!