How to Make It
Preheat oven to 425ºF. Toss squash with 2 tsp. oil; spread in a single layer on a foil-lined baking sheet. In a small bowl, whisk syrup, vinegar, mustard, 1/2 tsp. chili powder, 1/4 tsp. salt, cumin and 1/8 tsp. cayenne. Drizzle in 3 Tbsp. oil, whisking.
Roast squash until golden on bottom, about 25 minutes. Turn squash; brush with 2 Tbsp. vinaigrette. Roast until golden on other side, about 10 minutes. Brush with 2 Tbsp. vinaigrette.
In a skillet, toss seeds with remaining 1 tsp. oil, 1/4 tsp. chili powder and pinch of salt and cayenne. Stir over medium heat until toasted, 5 to 8 minutes.
Toss greens with cranberries; arrange on 4 plates. Drizzle with vinaigrette, sprinkle with seeds, top with squash and serve.