Preheat oven to 425° F.
Cut off the ends of the squash. Carefully cut the squash in half lengthwise. Scoop out the seeds, then cut squash into 1/2 inch pieces.
Place squash pieces into a large bowl and toss in avocado oil, salt and pepper, and spread onto a baking sheet. Bake squash until golden brown, about 20-30 minutes, turning halfway through.
In a separate bowl, combine cranberry sauce, balsamic vinegar, dijon mustard, olive oil, and a pinch of black pepper. Either whisk or use an immersion blender to blend until smooth. Set aside.
In 4 bowls, place 2 cups of greens in each. Top with delicata squash, goat cheese, pumpkin seeds, and dried cranberries. Drizzle with dressing.