Preheat oven to 400° Fahrenheit (200° Celsius). Line a rimmed baking sheet with parchment paper. Place squash on one half of sheet, toss with 1 tablespoon (15 mL) of oil, a pinch of salt and some pepper.
Roast for 10 minutes, remove from heat and flip squash. In a medium bowl, toss bread with 1 tablespoon (15 mL) of oil, salt and pepper and place on baking sheet with squash. Roast for 10-12 minutes more until squash is tender, and bread is toasted and crisp at the edges. Remove from heat and set aside.
Meanwhile, to a jam jar, add oil, balsamic, lemon juice, garlic, Dijon, maple syrup salt and pepper. Place lid on and shake up.
Place kale in a salad bowl. Drizzle over a third of the dressing and massage kale until it softens and wilts a bit.
Top with toasted bread, squash, onion, pomegranate and cranberries. Drizzle with a bit more dressing, and serve with remaining dressing.
Will keep, covered, in the fridge for up to 2 days.