Preheat oven to 400 degrees Fahrenheit.
Toss the cubed butternut squash with 2 tablespoons olive oil, salt, and pepper on a rimmed baking sheet.
Roast for 20 to 25 minutes or until tender and lightly browned, then remove from oven and let cool.
In a small bowl or jar, whisk together apple cider vinegar, Dijon mustard, maple syrup, and 0.33 cup olive oil until emulsified.
In a large salad bowl, combine the baby kale, arugula, and apple slices.
Add the cooled roasted squash, dried cranberries, and toasted pecans to the bowl.
Drizzle with the vinaigrette and toss gently to coat the ingredients evenly.
Sprinkle crumbled goat cheese over the top and serve immediately.