Preheat oven to 400°F. Line two baking sheets with parchment paper and set aside.
On one of the baking sheets, arrange the cubed butternut squash on top. Toss squash with 1 tablespoon oil and a pinch of salt, until evenly coated. Spread out so there is an inch or so between the squash cubes. Roast in the oven for about 30 minutes, until fork tender. Set aside to cool.
In a small bowl, combine the pecans, 1 tablespoon olive oil, 1 tablespoon pure maple syrup and a pinch of salt. Toss until evenly coated. Spread pecans out on the second baking sheet, allowing a few inches of space between each pecan. Bake in the oven for 5-7 minutes, keeping a close eye to make sure they do not burn. They will be slightly darker in color and fragrant when they are done. Remove from the oven and set aside.
Prepare the dressing by combining everything in small food processor or bowl (if you choose to mince the shallot by hand). Whisk until smooth. Add salt & pepper or more dijon/vinegar, to taste.
In a large bowl, add the chopped kale leaves. Pour the dressing over top. Using your hands, massage the dressing into the kale. Add the roasted squash, dried cranberries, crumbled cheese, and maple pecans. Toss to combine. Serve and enjoy!