Preheat oven to 400°F and line a baking sheet with parchment paper. Slice kabocha squash into wedges or cubes and toss with oil, salt, and cinnamon. Place on the lined baking sheet. Roast squash for roughly 20 minutes, or until fork tender. Remove and set aside.

In a blender, combine all dressing ingredients and blend until smooth. If too thick, add more oil, 1 tablespoon at a time, or a bit of water.

Place pecans on a baking sheet and toast in the oven for 5-7 minutes, tossing halfway through, watching to avoid burning.

Massage kale with olive oil for 1-2 minutes.

In a large bowl, add kale, roasted squash, pomegranate seeds, and toasted pecans. Top with dressing and toss to combine.