Preheat your oven to 400°F (200°C). Line a baking sheet with parchment paper.
Toss sweet potato cubes with 2 tablespoons olive oil, salt, and pepper. Spread them evenly on the baking sheet.
Roast sweet potatoes for 25-30 minutes, flipping halfway through, until tender and slightly caramelized.
While the potatoes roast, massage the chopped kale with a tiny bit of olive oil and a pinch of salt for about 1 minute to soften it.
Toast pepitas in a dry skillet over medium heat until fragrant, about 3-4 minutes.
Whisk together all dressing ingredients in a small bowl until well combined.
In a large bowl, combine the massaged kale, roasted sweet potatoes, sliced red onion, toasted pepitas, and dried cranberries.
Pour the dressing over the salad and toss well to combine.