Remove tough stems from the kale and stack leaves. Roll or chiffonade and chop into roughly 1-inch pieces. Place chopped kale in a large bowl and sprinkle with a pinch of fine sea salt. Massage the kale with clean hands for 2–3 minutes until it darkens and softens.

Roast the butternut squash

Preheat oven to 425°F (220°C). Toss the cubed butternut squash with 2 tablespoons extra-virgin olive oil, 1 teaspoon kosher salt, and 1/2 teaspoon freshly ground black pepper on a rimmed baking sheet in a single layer. Roast for 20–25 minutes, turning once halfway through, until the edges are caramelized and cubes are tender. Remove from oven and let cool slightly.

Toast the almonds

While the squash roasts or after, heat a dry skillet over medium heat. Add 1/2 cup sliced almonds and toast, stirring frequently, until golden and fragrant, about 3–4 minutes. Transfer to a small bowl to cool (they will continue to crisp).

Assemble the salad

To the massaged kale, add the roasted butternut squash (warm or at room temperature), toasted almonds, and 1/2 cup dried cranberries. Toss gently to combine. Crumble or shave 1/2 cup Pecorino Romano over the salad and toss lightly.

Season and finish

Drizzle desired amount of the raspberry-walnut dressing over the assembled salad (start with about 3–4 tablespoons and add more to taste). Toss to coat evenly. Taste and adjust seasoning with fine sea salt and freshly ground black pepper as needed. Serve immediately.

Dressing (Raspberry & Walnut)

If using frozen raspberries, thaw and drain excess liquid. Place 1 cup raspberries and 1/4 cup walnut halves in a blender or food processor.

Add 2 tablespoons red wine vinegar, 1 tablespoon maple syrup (or honey), 1 teaspoon Dijon mustard, 1/4 teaspoon salt, and 1/4 teaspoon freshly ground black pepper to the blender.

With the blender running, slowly stream in 4 tablespoons extra-virgin olive oil until the dressing emulsifies and reaches a smooth, pourable consistency. Taste and adjust sweetness, acidity, or salt to preference. If you prefer a smoother texture, strain the dressing through a fine-mesh sieve to remove seeds and walnut bits; otherwise leave as-is for texture.

Transfer dressing to a jar and refrigerate until ready to use. Shake or whisk before serving.