Preheat the oven to 400°F (200°C). Line a baking sheet with parchment paper.

On the prepared baking sheet, toss the butternut squash half circles with 1 tablespoon of olive oil, cinnamon, cayenne pepper, and honey. Spread the squash evenly in a single layer. Roast for 20-25 minutes, flipping halfway through, until the squash is golden and tender.

While the squash roasts, toast the raw pepitas in a dry skillet over medium heat for 2-3 minutes, until lightly browned and fragrant. Set aside.

To prepare the pomegranate vinaigrette, heat the remaining 1 tablespoon of olive oil in a small skillet over medium heat. Add the shallots and sauté for 2-3 minutes until softened. Stir in the chopped sage and cook for another 1-2 minutes.

Remove the skillet from the heat and stir in the pomegranate juice, balsamic vinegar, honey, and a pinch of crushed red pepper flakes. Season with salt and pepper to taste. Let the dressing cool slightly.

In a large bowl, combine the shredded kale and Brussels sprouts. Toss with the roasted butternut squash, toasted pepitas, and pomegranate arils.

If using, slice the fresh figs and add them to the salad. Drizzle the pomegranate vinaigrette over the salad and toss to combine.

Top with shredded gouda cheese just before serving.