Preheat the oven to 400°F. Cut the top off the head of garlic to expose the cloves and drizzle with 1 tablespoon of olive oil. Wrap it in aluminum foil and roast in the oven for about 30-35 minutes, until soft and fragrant. Allow to cool slightly, then squeeze the roasted garlic cloves into a bowl and mash with a fork.
In a large mixing bowl, combine the chopped kale, remaining tablespoon of olive oil, salt, and black pepper. Massage the kale with your hands for about 2-3 minutes until it becomes tender and slightly wilted.
Add the mashed roasted garlic, Parmesan cheese, Caesar dressing, and lemon juice to the kale. Toss everything together until the kale is evenly coated.
Serve the salad topped with croutons and additional Parmesan cheese if desired.