When roasted pumpkin is tender but not completely soft, after 30 minutes, remove from oven. Turn oven to broil.
Cut pumpkin into 2-inch wedges; poke sage leaves into flesh. Drizzle with olive oil and season with salt and pepper. Broil until wedges are sizzling and sage is crisped, about 6 minutes. Serve drizzled with additional oil, if desired.