Heat a large skillet over medium low heat and add the pine nuts. Toast them in the hot skillet for about 5 minutes, just until slightly golden brown. Move them around in the pan as they toast to avoid over-browning. Remove them to a plate to cool.
Turn the heat up to medium-high and add the olive oil.
Add the cubed butternut squash and saute for about 10 minutes, turning the pieces as they begin to brown and soften. Add the maple syrup after about 5 minutes, and turn the heat down to medium to prevent the syrup from burning.
While the squash cooks, massage the 1 teaspoon of olive oil into the kale leaves and place the kale in a large serving bowl.
Once the squash is caramelized and soft, add it on top of the kale along with the cooked and crumbled bacon and the toasted pine nuts.
To make this salad ahead, simply prepare all the components, store separately, and assemble right before serving. Reheat the squash in the microwave or in a skillet on the stove before serving.