Preheat oven to 400°F (200°C). Toss cubed butternut squash with 1 tbsp olive oil, salt, and pepper on a sheet pan and roast for 18-20 minutes until golden and tender.
Place chopped kale in a large bowl with a drizzle of olive oil and a pinch of salt; massage gently with your hands for 1 minute until softened.
In a small jar, shake together the olive oil, apple cider vinegar, maple syrup, Dijon mustard, salt, and pepper until emulsified.
Top the kale with roasted butternut squash, sliced apples, pomegranate arils, and candied pecans. Drizzle with vinaigrette, toss gently, and finish with crumbled goat cheese.