In a dry skillet over medium-high heat, toast the pumpkin seeds for about 3 minutes until browned and fragrant. Set aside.
In a large saucepan, heat the olive oil over medium heat. Add onion and sauté until translucent, about 5 minutes. Add garlic and chopped chilies; sauté for 2 minutes. Add brown sugar, cumin, red chili flakes, salt, and pepper and sauté for another minute. Add pumpkin, chicken or vegetable stock, and coconut milk. Stir well. Reduce heat and cook until heated through, 5 – 10 minutes.
Process in a blender in batches until smooth. (Make sure you remove the center piece from the blender lid so that the soup does not explode in the blender.)