Preheat your oven to 400°F (200°C). Line a large baking sheet with parchment paper.
Place the sliced delicata squash on the baking sheet. Drizzle with 2 tablespoons of olive oil and sprinkle with salt and pepper. Toss to coat evenly and spread in a single layer.
Roast the squash for 20 to 25 minutes, flipping halfway through, until the edges are golden brown and the squash is fork-tender. Remove from the oven and set aside to cool slightly.
While the squash roasts, place the pecan halves in a small skillet over medium heat. Toast for 3 to 5 minutes, stirring frequently, until fragrant and slightly darkened. Remove from heat and roughly chop once cooled.
In a small jar or bowl, whisk together the 1/4 cup extra virgin olive oil, apple cider vinegar, maple syrup, and Dijon mustard until emulsified. Season with a pinch of salt and pepper to taste.
Place the chopped kale in a large mixing bowl. Drizzle with 2 tablespoons of the prepared dressing. Use your hands to massage the kale for 2 to 3 minutes until the leaves are dark green, tender, and reduced in volume.
Add the roasted squash, sliced apples, dried cranberries, and toasted pecans to the bowl with the kale.
Drizzle the remaining dressing over the salad and toss gently to combine.
Top with crumbled goat cheese just before serving to maintain texture.