Preheat your oven to 400°F (200°C). Spread the cubed squash on a baking sheet, drizzle with olive oil, and toss to coat evenly. Roast for about 25-30 minutes, until the edges are caramelized and the squash is tender.
While the squash roasts, place the sage leaves in a dry skillet over medium heat. Toast them until crisp and fragrant, about 2-3 minutes, then remove and set aside to cool.
Once the squash is roasted, transfer it to a large mixing bowl. Gently toss with apple cider vinegar, salt, and pepper to taste, allowing the flavors to meld.
Chop the toasted sage leaves coarsely and sprinkle them over the squash, mixing gently to distribute the crispy herbs evenly throughout the dish.
Serve the salad warm or at room temperature, highlighting the tender, caramelized squash contrasted with the fragrant sage and bright vinegar.