Roast the squash. Heat the oven to 400°F. Toss the cubed squash with 1 tablespoon olive oil and spread on a parchment-lined baking sheet. Roast for 20–25 minutes, tossing halfway through, until tender and lightly caramelized. Let cool slightly.
Cook the bacon. Place the chopped bacon in a skillet over medium heat. Cook, stirring occasionally, until crisp. Transfer to a paper-towel-lined plate.
Toast the pecans. Toast in a dry skillet over medium-low heat for 3–5 minutes, stirring frequently, until fragrant. Set aside to cool.
Make the dressing. Whisk together the maple syrup, Dijon, garlic, orange vinegar, salt and pepper. Slowly whisk in the olive oil until emulsified. Taste and add a little more vinegar if you prefer a tangier dressing.
Massage the kale. Place the washed, thoroughly dried kale in a large bowl. Add 2 tablespoons of the dressing and massage with clean hands for 1–2 minutes, until the leaves soften and deepen in color.
Assemble. Add the squash, apple, pomegranate, pecans and bacon. Toss gently with enough of the remaining dressing to coat. Let stand for 5–10 minutes before serving.
Make-ahead tip: Roast the squash and prepare the dressing ahead of time. Add the apple, pecans and bacon shortly before serving for the best texture.