Pre-heat oven to 425 degrees.
Peel squash and cut into 1/2- to 3/4-inch cubes.
Line two rimmed baking sheets with foil or parchment.
In a large bowl, toss the squash with olive oil, salt, and pepper to evenly coat the cubes.
Divide the squash evenly between the two baking sheets and spread into an even layer with as much space between cubes as possible. This allows the cubes to brown on the edges. If they are too close together the squash will steam and become mushy.
Bake 35-40 minutes, switching the positions of the pans and rotating each pan. When cubes crisp up on the bottom, loosen them gently with a metal spatula and flip them over so the other side can get crispy.
Cut kale into thin ribbons, removing stems.
Toss kale, almonds, pomegranate seeds, cheese, and squash in serving bowl. For firmer kale you may choose to wait for squash to cool before tossing.