Preheat the oven to 400 degrees and arrange two evenly spaced oven racks.
Spread the cornbread and the corn onto two separate sheet pans. Drizzle the corn with the olive oil and toss to combine. Sprinkle each sheet pan lightly with salt and pepper. Roast for 15 minutes, tossing the cornbread and corn halfway through. Set aside to cool.
Meanwhile, chiffonade the kale: cut along each side of the rib to remove the leaves on each side. You should end up with two long strips from each rib. Roll the leaves lengthwise into "cigars" and slice them thinly crosswise to cut the kale into ribbons. Wash the kale and dry it using a salad spinner.
To assemble the salad, pour the dressing over the kale and toss well. Add the corn and croutons, and the Pecorino, and toss again. Serve immediately or refrigerate for up to several hours.