Pre-heat oven to 400 degrees and line a baking sheet with foil.
Toss butternut squash cubes with olive oil, salt, and pepper on prepared baking sheet.
Bake squash for about 25 minutes, until tender and starting to brown. Toss once halfway through baking. Remove from oven and let cool.
In a large bowl, pour cranberry dressing over kale. Gently massage dressing into kale for a couple minutes.
Evenly divide kale into two smaller bowls. Divide chopped hardboiled egg, pomegranate arils, diced avocado, crumbled gorgonzola, and crumbled bacon on top of kale in two bowls.
Drizzle additional cranberry dressing on salad if desired.