Preheat the oven to 425 F. Add the butternut squash and brussels sprouts to a baking sheet. Add 1 tbsp olive oil and salt and pepper and toss to combine. Transfer to the oven and cook for 20-30 minutes, until the veggies are starting to brown.
When the veggies have about 10 minutes left, add the bread to another baking sheet and toss with 1 tbsp of olive oil and salt and pepper. Transfer to the oven and bake for 10 minutes, until bread is golden brown.
While the veggies and bread are cooking, prep everything else. Thinly slice the red onion. Make the dressing by adding all the ingredients to a bowl and whisk until smooth.
To assemble, add the kale, butternut squash, brussels sprouts, red onion, bread, parmesan, and pomegranate seeds to a bowl. Pour the dressing over everything and toss until combined. Serve and enjoy!