Preheat oven to 425°F. Toss cubed squash with 2 tsp olive oil, salt, and pepper. Roast for 30–35 minutes, stirring halfway, until golden and tender.
Heat 2 tsp olive oil in a skillet. Add shallots and salt; cook 15 minutes until caramelized. Add garlic, balsamic vinegar, and sage; cook 2 more minutes.
Mix roasted squash with caramelized shallots and cranberries.
Top with crumbled goat cheese and chopped pistachios. Bake for 10–15 minutes until cheese softens.
Garnish with sage and fresh pepper. Serve warm.
