In a large dutch oven, heat olive oil over medium heat. Add onion, carrot and garlic and cook for 3-4 minutes.
Add the pumpkin, thyme, salt, black pepper, cumin, ginger, nutmeg and cayenne. Cook over medium-low heat for an additional 3-4 minutes.
Add the vegetable broth and cook for 3-4 minutes, stirring frequently.
Stir in the maple syrup. If a smoother texture soup is desired, transfer to a blender or Vitamix. Puree until it reaches your desired consistency. Return the puree back to the dutch oven and check for seasoning.
If a creamier texture is desired, add in 1 tablespoon of heavy cream at a time until the desired consistency is reached.
Garnish with grilled cheese croutons, extra cream and flakey sea salt, if desired.