Preheat oven to 400F. In a small bowl combine avocado oil, salt, and pepper.
Cut ends off butternut squash and halve. Scoop out seeds. Brush flesh of squash with seasoned avocado oil. Place cut side down on a baking sheet and bake until fork tender, about 30 minutes. Once cool enough to handle, scoop out flesh, and discard skin.
Meanwhile heat olive oil in an ovenproof skillet over medium-high heat. Add garlic and cook until fragrant. Add kale and cook, tossing, until kale begins to wilt and garlic is golden. Add raisins and roasted squash to skillet and fold until well mixed.
Cover mixture with breadcrumbs and sprinkle with both cheeses. Transfer pan to oven and bake until cheese is golden and bubbly, about 20 minutes. Serve.