Cut the squash lengthwise and scoop out the seeds. Flip onto a flat surface, flesh side down, and slice into small half moons, about 1/2" thick. Chop each half moon into 4 pieces and add to a large mixing bowl.
To that bowl, add your brussel sprouts and drizzle with olive oil. Season with salt and pepper and toss to combine.
Transfer veggies to a baking sheet and roast for 25 - 35 minutes until squash has softened. Remove and let cool for 10 - 15 minutes.
While the veggies are cooling, gently steam the kale, 60 seconds. Strain and transfer to the mixing bowl. Add the veggies and quinoa and toss to combine.
Whisk together the dressing ingredients (or better yet, add them to your blender) until completely smooth. Pour over the salad and toss to evenly coat. Sprinkle in pepitas.
Taste and adjust seasonings as desired. Serve immediately.