Preheat your oven to 400 degrees f, and toss the delicata squash in olive oil, salt, and red pepper flakes until fully coated. When oven is preheated, cook for 10 minutes, then flip over each slice and cook for an additional ten minutes or until browned to your liking.
In a pan on medium heat, add the butter or an additional drizzle of olive oil. When heated, add the julienned red onion and cook until caramelized and slightly brown. Set aside to cook.
Combine all of the ingredients for the dressing but the olive oil in a blender and blend on high speed until fully combined. Then, turn the blender down to a lower speed and slowly drizzle in olive oil to emulsify it and make the dressing thick. After all olive oil has been added, blend for an additional 30 seconds.
Toss the dressing and butter lettuce in a large bowl, then add the quinoa, caramelized onions, chicken, and cucumber until combined. Then add the rest of the ingredients except the pomegranate seeds and the goat cheese and gently toss as to not break the pears or smush the avocado chunks.
Top with pomegranate seed and goat cheese, then serve.