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Preheat oven to 400°F. Line a baking sheet with parchment paper.
Toss the squash with the olive oil, maple syrup, salt and cinnamon. Place on a baking sheet and roast until tender (about 20 minutes), flipping the slices halfway through. In the last 3 minutes of roasting add the pumpkin seeds to the sheet pan.
Meanwhile in a large bowl, whisk together the olive oil, vinegar, pomegranate molasses, mustard, shallot, salt and pepper.
When the squash is tender and pumpkin seeds are toasted remove baking sheet from oven and set on wire rack to cool.
Meanwhile toss the kale with the vinaigrette using your hands to gently massage and soften the kale. Top with the squash, persimmon slices, pomegranate seeds and toasted pumpkin seeds.
Serve immediately.