Preheat the oven to 400 degrees F. Line a baking sheet with parchment paper. Peel the kabocha squash and chop into bite-sized pieces. Toss in enough olive oil to well coat the pieces. Lay them out on the parchment paper.
Combine the brown sugar, coffee and cacao nibs together in a spice grinder and grind together for 15 seconds. Sprinkle over the kabocha pieces. Roast for 10 minutes or until tender. Remove and set aside.
Remove the center stem of the kale leaves and tear the leaves into smaller pieces. Thoroughly wash and dry. Add to a large bowl.
Slice the fuyu persimmon into slices and add to the bowl along with the cheddar cheese, pumpkin seeds, and pomegranate seeds.
Combine all the ingredients for the dressing and mix well. Toss the squash in 2 tablespoons of the dressing. Add the rest of the dressing to the salad in the bowl and toss. Add the squash pieces and lightly toss again.
This is best served while the squash is still warm.