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Add the olive oil to a large stock pot over medium-high heat. Once it's hot and shimmering, add the diced onion and saute for 2-3 minutes until transluscent.
Stir in the squash, carrots, vegetable broth, and apple juice. Bring them all to a boil over high heat then turn the heat down to low and simmer, uncovered, for 15 minutes. The squash and vegetables should be fork-tender.
Stir in the pumpkin puree, butter, cream cheese, heavy cream, all of the spices, and maple syrup. Stir well until the cream cheese is melted into the soup.
Carefully transfer the soup to a large, high-speed blender. I like to spoon out the veggies and then carefully pour the broth in next. Blend on high speed until it's smooth and creamy and no chunks remain. Alternately, keep the soup in the pot and use a handheld immersion blender.
Carefully pour the soup back into the stock pot. Serve immediately with a drizzle of cream, pumpkin seeds, and a dash of cinnamon. Soup stays fresh in an airtight container in the fridge for up to 5 days.