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Preheat oven to 375°. Wash the outside of the kabocha squash with warm water. Cut the squash in half and scoop out all the seeds. Cut the squash into 1-inch semicircles. Toss the squash pieces with oil, sprinkle with sea salt and spread on a roasting pan.
Roast the squash for 15 minutes, remove from oven to toss, then roast for another 10-15 minutes, or until tender and golden.
While squash is roasting, prepare the dressing by placing all ingredients except the olive oil in a small bowl. Whisk until combined, then slowly whisk in the olive oil. Set aside.
To prepare the salads, place a portion of the kale on a plate, top with a portion of cranberries, pepitas and feta. Add the roasted kabocha slices, drizzle with desired amount of dressing and serve.