Evenly coat insides of pumpkin wedges with 1 tablespoon olive oil. Season with salt and pepper to taste. Place pumpkin wedges cut side-down on baking sheet and roast at 400F 40-45 minutes or until pumpkin is very tender when pierced with a fork.
Once pumpkin is cool enough to handle, peel off skin and discard. Set pumpkin aside in a bowl.
In a Dutch oven or large pot, heat remaining 1 tablespoon olive oil over medium-high heat. Add Italian sausage and cook 3-5 minutes until browned. Transfer to a medium bowl and set aside.
In remaining pan drippings over medium-high heat, saute onion and carrots until tender, about 3-5 minutes. Add garlic and nutmeg if using and saute 1 additional minute until fragrant.
Add chicken broth and pumpkin to pot and bring to a simmer over medium-high heat. Remove soup from heat and use an immersion blender or transfer in batches to a regular blender to blend soup on high 30-60 seconds until very smooth.
Pour blended soup back into pot and bring to a simmer over medium-high heat. (if soup seems too thick from pumpkin, thin with a little extra chicken broth as needed)
Remove soup from heat and add thyme, tortellini, sausage, whipping cream, and kale. Let soup stand 5 minutes until kale is wilted. Season soup with additional salt and pepper to taste and serve warm. Enjoy!