Preheat the oven to 400°F. Line a rimmed baking sheet with parchment paper.
Slice the squash in half and scrape out the seeds. Cut the squash into ½-inch slices and toss with the 2 tablespoons of oil, salt, and cinnamon. Place the squash on the lined baking sheet and roast for 40 minutes, until fork-tender. Once done, let cool for 5 to 10 minutes. (There’s no need to peel the skin of kabocha squash; it’s edible!)
While the squash is roasting, massage the kale with the 1 tablespoon of oil for 1 to 2 minutes, until evenly coated. Set aside.
In a small sauté pan over medium-low heat, toast the pecans until lightly browned and fragrant, about 5 minutes, stirring often to ensure that they don’t burn.
Make the dressing: Place all of the ingredients in a blender and blend until smooth.
Assemble the salad: Divide the kale between two plates or place it in a large serving bowl. Top with the roasted kabocha squash, pomegranate seeds, and toasted pecans. Dress the salad with as much dressing as you’d like and serve immediately.
Notes
You can also use 2 acorn squash (since they’re smaller) or 1 large butternut squash in this recipe! If using either of these two squashes, peel them and then roast as directed in Step 2.You can store the dressing in a closed container in the refrigerator for up to 1 week.