Preheat oven to 425°F and line two sheet pans with parchment paper if desired.
Roast the squash: Toss squash with olive oil, salt, pepper, and smoked paprika. Spread on a sheet pan and roast for 20–25 minutes, flipping halfway through, until tender and caramelized.
Crisp the quinoa: Spread cooked quinoa on a second sheet pan. Toss with a little olive oil and salt. Roast for 10–12 minutes, stirring once, until lightly crisp.
Prepare the kale: Add chopped kale to a large bowl. Drizzle with olive oil and a pinch of salt. Massage for 30–60 seconds until softened.
Assemble the salad: Add fennel, pomegranate arils, pecans, and cheese to the kale. Toss gently.
Finish and serve: Add roasted squash and crispy quinoa. Drizzle with maple Dijon vinaigrette and toss lightly. Adjust dressing to taste and serve.
