Preheat the oven: Preheat the oven to 400°F.
Season the squash: Toss the cubed butternut squash with olive oil, salt, and pepper, then spread it in a single layer on a baking sheet.
Roast: Roast for 20 to 25 minutes, until tender and golden. Let cool slightly.
Start the dressing: In a small bowl, combine the garlic, lemon juice, chopped anchovies, and salt. Let it sit for 5 minutes.
Finish the dressing: Whisk in the mayonnaise, Worcestershire sauce, pepper, and Parmesan until smooth. Refrigerate until ready to use.
Massage the kale: Massage the chopped kale with a squeeze of lemon juice and a pinch of salt for 2 minutes, until tender.
Toss the greens: In a large bowl, toss the kale and romaine with half the dressing.
Add the toppings: Add the roasted squash, sliced pears, pomegranate seeds, red onion, toasted pumpkin seeds, and half the Parmesan. Toss gently.
Top and serve: Transfer to a serving bowl and top with the remaining Parmesan and an extra drizzle of dressing, if desired. Serve chilled or at room temperature.