Combine all the ingredients for the dressing in a mason jar and shake until combined. Set aside.
Heat a large non-stick skillet over low heat.
Add the pine nuts to the heated skillet and toast them until they’re just barely brown, using a wooden spoon to toss them around the pan while they’re toasting.
Remove the toasted pine nuts to a plate and set aside.
Heat the same skillet over medium heat. Dice the pancetta and add it to the heated skillet, cooking it until it’s slightly crispy.
Set the pancetta aside and drain the fat from the pan, reserving about 1 tablespoon of fat in the pan.
Keep the pan over medium-low heat and add the chunks of butternut squash and the maple syrup. Toss the butternut squash in the remaining pancetta fat and the maple syrup and fry it until the chunks are caramelized on all sides (flip every 3-4 minutes).
While the butternut squash is caramelizing, wash and dry the kale, ripping the leaves off the stems and arranging them on plates for individual servings or in a large bowl to serve the salad family-style.
Remove the butternut squash from the pan, arranging it over the kale immediately so the kale wilts slightly.
Sprinkle the toasted pine nuts and the crispy pancetta over the kale and the butternut squash, and finish off the salad with a drizzle of the maple vinaigrette dressing.
Serve immediately.