Roast the butternut squash. Preheat the oven to 425°F. Toss the cubed butternut squash with 1 tablespoon olive oil, salt, and pepper. Spread onto a parchment-lined baking sheet and roast for 35-40 minutes, tossing halfway through, until tender and caramelized.

Cook the bacon and sage. While the squash roasts, cook the bacon in a large skillet over medium heat until crispy. During the last minute, add the fresh sage leaves to the bacon grease and let them crisp up. Transfer the bacon and sage to a paper towel-lined plate. Once cooled, chop the bacon and crumble the sage.

Cook the orzo. Remove all but about 1 tablespoon of bacon grease from the skillet. Add the chopped shallot and cook for 2–3 minutes until softened. Add the garlic and cook for another 30 seconds. Stir in the dry orzo and toast for 1 minute. Pour in the chicken stock, bring to a simmer, and cook for 10–12 minutes, stirring frequently, until the orzo is tender. Add a splash of extra stock or water if needed.

Prepare the kale. Add the chopped kale to a large serving bowl. Drizzle with a small amount of the vinaigrette and massage for about 1 minute to soften the leaves.

Make the vinaigrette. Whisk together the olive oil, apple cider vinegar, thyme, rosemary, ground sage, salt, and pepper until combined.

Assemble the salad. Let the cooked orzo cool slightly, then add it to the bowl with the kale. Add the roasted butternut squash, crispy bacon, parmesan, pecans, pomegranate seeds and vinaigrette. Toss everything together until evenly coated.

Finish and serve. Top with extra parmesan. Serve warm, at room temperature, or chilled!