Preheat the oven to 425 degrees F. Peel the sweet potatoes and cut them into 1/2-inch dice and transfer to a large bowl. Cut the shallot halves into thin slices and add to the bowl along with the oregano.
Season with salt and pepper, drizzle about 1 tablespoon of olive oil over the sweet potato mixture and toss to coat.
Spread the mixture in a single layer on an oiled rimmed baking sheet and bake for 30 minutes or until the potatoes are tender and lightly browned, turning once about halfway through.
Roll the kale leaves into a tight roll and cut crosswise into thin ribbons. Transfer to a bowl, drizzle with a little olive oil and season with salt and pepper.
Spread the kale on an oiled baking sheet and place in the oven when the sweet potatoes are about halfway done roasting until the kale is crisp and lightly browned, about 15 minutes.
To serve, transfer the sweet potatoes to a bowl, add the nuts, cranberries, and kale and sprinkle with a few grinds of black pepper. Toss gently to combine. Serve hot.