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Preheat oven to 450 degrees F.
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Spread the raw chicken breasts evenly with pesto and refrigerate at least 6 hours.
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Toss the squash only with 1 tablespoon olive oil and season with sea salt and black pepper as desired. Evenly spread out in a 9x13" cookie sheet. Roast for 15 minutes.
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In the meantime, toss mushrooms with remaining olive oil and season with sea salt and black pepper as desired. When the timer goes off, mix the mushrooms with the squash and roast for 15 more minutes or until tender and beginning to brown.
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In a large skillet, over medium heat, heat the chicken until cooked through, about 6 minutes per side. There is no need to add olive oil to the skillet as the pesto has sufficient fat to properly sear the chicken.
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In a large bowl, toss the kale, squash and mushroom mix, pumpkin seeds, goat cheese, and dressing to combine. Top with cooked chicken and serve.