Cut the butternut squash into 1 inch (approximately) cubes. Toss with 1-2 tablespoons of olive oil and spread on a large baking sheet. Sprinkle with salt and pepper to taste. Place both the seeds and the squash in the oven. Take the seeds out of the oven after they are golden brown and crispy, about 10-15 minutes. Watch them carefully in they can burn quickly. Reserve seeds in a small bowl lined with a paper towel.

Continue baking the squash for about 25-35 minutes more (for a total of 35-45 minutes), flipping the cubes over halfway though. Remove the squash from the oven when it is tender when pierced with a knife and is golden brown on the edges. Place 1 cup of the roasted squash on a platter or a shallow salad bowl. Reserve the rest for another use.

While the squash is cooking, prepare the kale by tearing the leaves from the main stem that runs down the center of the leaves. Discard the stem. Rinse the kale and squeeze out any excess moisture. Heat a large skillet over high heat. Drizzle the pan lightly with olive oil, about 1 tablespoon. Add the kale and cook, stirring frequently, until the kale wilts slightly and becomes a bright green color, about 2-3 minutes. Add it to the platter with the squash.

Make the dressing. Whisk the shallot, maple syrup and Dijon together in a small bowl. Whisk in the oil and vinegar until emulsified. Add salt and pepper to taste.

Toss the butternut squash and the kale with a bit of the dressing, using only enough to lightly coat the leaves. You will probably have some dressing leftover. Top the salad with the reserved roasted squash seeds. Serve at room temperature or chilled.