Preheat the oven to 400 F.
Toss brussels and butternut squash with olive oil, red chili powder, dry rosemary, salt, and pepper. Roast for 40-45 minutes. You can take the brussels out at 20-25 minutes if you want to retain their crunch, but you don’t have to take them out.
Cut sourdough into 1-inch cubes. Cook in a large pan with 1 tbsp olive oil on medium-low heat for about 10 minutes, or until nicely toasted. Toss occasionally. Alternatively, bake in a sheet pan for 10 minutes at 400 F.
Toast the pumpkin seeds with cinnamon and sea salt over medium heat until golden and crunchy, so about 5-6 minutes.
For the vinaigrette, finely chop a shallot. Add ½-1 tbsp olive oil to a small pan and caramelize the shallots until crisp and browned. Add to a jar with the rest of the ingredients for the vinaigrette. Shake the jar until the dressing comes together. Add salt and pepper to taste.
Assemble! Add bread, roasted veggies, and greens to a large bowl. Toss. Add pomegranate seeds, pumpkin seeds, and the vinaigrette. You can enjoy it immediately, but ideally, set some aside for a couple of hours to let the bread soften and the flavor soak in.