Preheat oven to 450 degrees F. Place squash in a shallow baking pan. Drizzle with 1 Tbsp. olive oil; sprinkle with 1/2 tsp. salt and 1/4 tsp. black pepper. Roast 10 minutes; turn over. Roast 10 minutes more or until brown and tender. Remove squash; set aside pan. Reduce oven to 400 degrees F.
Meanwhile, wash seeds in cold water to remove all pulp; pat dry. In same baking pan toss together seeds, 1 tsp. olive oil, 1/8 tsp. salt, and 1/8 tsp. black pepper. Bake 5 minutes or until toasted.
For pickled raisins: In a small microwave-safe bowl combine raisins, vinegar, and 1 Tbsp. water. Microwave on high 1 minute or until bubbly. Let cool.
For Miso-Lemon Vinaigrette: In a bowl whisk together lemon juice, miso paste, and garlic until smooth. Whisking constantly, gradually add remaining 1/4 cup olive oil until emulsified.
In a large bowl toss kale, squash, and fennel with Miso-Lemon Vinaigrette. Place on platter. Spoon raisin mixture over; top with toasted seeds.