Preheat oven to 400°F (200°C). Spread butternut squash on a baking sheet, drizzle with olive oil, season with salt and pepper, and roast 20–25 minutes until tender.
In a small bowl, whisk olive oil, vinegar, maple syrup, Dijon mustard, salt, and pepper to make vinaigrette.
Place kale in a large bowl. Massage with a drizzle of vinaigrette for 1–2 minutes to soften.
Add roasted squash, apple slices, cranberries, pecans, and goat cheese to the kale.
Pour remaining vinaigrette over salad and toss gently to combine.
Serve immediately, or chill briefly for deeper flavor.
Notes
Swap pecans for walnuts or pumpkin seeds. For a heartier salad, add roasted chicken or quinoa. Best enjoyed fresh.