On a large, rimmed baking sheet, toss the squash with the olive oil and season with salt and pepper. Roast for 30 minutes, stirring occasionally, or until the squash is tender and beginning to brown.
Meanwhile, cook the rice according to package directions.
In a large bowl, drizzle a few drops of olive oil over the kale. Massage the oil into the kale with your hands until it feels softer and looks darker.
In low, wide dinner bowls, evenly divide and layer the rice, squash, kale, cabbage, tomatoes, avocados, cucumber, and cashews.
Top with the creamy cashew dressing and toss to combine.