Preheat the oven to 400 degrees F. Spread the butternut squash cubes on a baking sheet, drizzle with 2 tablespoons olive oil, and sprinkle with salt and pepper. Toss to coat evenly.
Roast the squash for 25 to 30 minutes, stirring once halfway through, until the edges turn golden and the pieces soften.
While the squash roasts, place the kale in a large bowl. Add the remaining 1 tablespoon olive oil and massage the leaves for 2 minutes until they darken and soften slightly.
In a small bowl, whisk together the balsamic vinegar and honey until smooth.
Add the warm roasted squash to the kale. Drizzle the dressing over the top and toss gently to combine.
Sprinkle the pumpkin seeds and dried cranberries over the salad just before serving.