Preheat oven to 400°F (200°C). Line a baking sheet with parchment paper.
Toss the butternut squash cubes with 1 tablespoon olive oil, salt, and pepper. Spread on a shallow baking sheet. Scatter 5 sage leaves among the squash. Roast for 40-45 minutes, flipping once, until the cubes are golden and tender.
Finely chop the remaining 5 sage leaves.
About 15 minutes before the squash is done, in a large pot or deep skillet, heat the remaining 1 tablespoon olive oil over medium heat. Add chopped sage, chopped shallots and minced garlic; cook over low heat for 2-3 minutes until softened and fragrant.
Pour in 6 cups of the gluten-free stock. Add chopped kale (letting it wilt). Bring to a simmer. Then stir in the orzo. Cook according to the orzo package instructions until al dente, stirring frequently. If it looks too thick or dry, add additional stock or water as needed to reach a creamy, risotto-like consistency.
Once orzo is cooked, remove from heat. Stir in grated Parmesan cheese until melted and the dish is creamy. Taste and adjust seasoning (salt, pepper) as needed.
Spoon orzo into bowls, top with roasted butternut squash cubes, extra sage leaves or garnish, and more Parmesan if desired. Serve immediately.