Heat the oven: Preheat to 425°F (220°C). Line a sheet pan with parchment for easy cleanup.
Prep the squash: Toss cubed squash with 1.5 tablespoons olive oil, 1/2 teaspoon salt, pepper, smoked paprika, and cumin.
Spread in a single layer on the sheet pan.
Roast until golden: Bake 20–30 minutes, flipping once halfway. You want browned edges and fork-tender centers. Set aside to cool slightly.
Toast the nuts: While the squash roasts, toast pecans in a dry skillet over medium heat for 3–4 minutes, stirring often, until fragrant.
Remove from heat.
Make the dressing: In a small bowl or jar, whisk olive oil, lemon juice, vinegar, Dijon, maple, garlic, salt, and pepper until emulsified. Adjust sweetness and acidity to taste.
Massage the kale: Place chopped kale in a large bowl. Drizzle with 1–1.5 tablespoons olive oil and a pinch of salt.
Massage with clean hands for 30–60 seconds until the leaves darken and soften.
Assemble: Add warm squash, toasted nuts, dried cranberries, and red onion to the kale. Drizzle with dressing and toss well. Taste and adjust salt, pepper, and lemon.
Finish with cheese: Sprinkle feta or goat cheese on top, if using.
Serve warm or at room temperature.