Preheat oven to 425 degrees Fahrenheit and line a rimmed baking sheet with parchment paper. Peel the butternut squash, cut it in half lengthwise, and scoop out the seeds.
Cut the squash into roughly 3/4 inch cubes, keeping pieces similar in size for even roasting. Spread in a single layer on the prepared baking sheet without overlapping.
Drizzle with 1 tablespoon olive oil and sprinkle generously with salt and pepper, tossing with hands to coat every piece. Roast for 22 to 25 minutes, flipping halfway through, until edges are golden brown and a fork slides in easily.
Remove from oven and set aside to cool slightly while preparing the rest of the salad.
Remove tough stems from the kale by holding the bottom of the stem and pulling the leafy part off. Tear or chop the leaves into bite sized pieces and add to a large mixing bowl.
Drizzle kale with remaining 1 tablespoon olive oil and a small pinch of salt. Using clean hands, massage firmly for 1 to 2 minutes, squeezing and rubbing until leaves darken slightly and feel noticeably softer. Set aside.
Add chopped pecans to a small, dry skillet over medium low heat. Toast for 3 to 5 minutes, stirring or shaking frequently, until fragrant and slightly darker in color.
Watch closely toward the end since nuts can burn quickly. Transfer toasted pecans to a plate to cool completely before adding to the salad.
In a small bowl or jar, combine balsamic vinegar, maple syrup, Dijon mustard, and minced garlic. Whisk until smooth and well combined.
While whisking continuously, slowly drizzle in 1/3 cup extra virgin olive oil until dressing is emulsified and slightly thickened. Taste and adjust with salt, pepper, or maple syrup as desired.
Add roasted butternut squash to the bowl with massaged kale. Scatter dried cranberries, toasted pecans, crumbled feta, and sliced red onion over the top.
Drizzle about three quarters of the balsamic vinaigrette over the salad. Toss gently but thoroughly with tongs or clean hands, making sure dressing coats the kale and squash evenly.
Taste and add remaining dressing if desired. Transfer to a serving bowl or platter and serve right away, or chill for later.