Heat the olive oil in a large Dutch oven over medium-high heat. Add the beef and brown it on all sides for about 6 minutes. Remove the beef to a plate.
Lower the heat to medium. Add the onion and cook until softened, about 5 minutes. Stir in the garlic and cook for 1 minute more.
Return the beef to the pot. Sprinkle in the cumin, smoked paprika, and cinnamon. Stir to coat the meat and cook for 1 minute until fragrant.
Add the butternut squash cubes and beef broth. Season with salt and pepper. Bring the mixture to a simmer, then cover and cook for 45 minutes until the beef is tender and the squash is soft.
Scoop out 2 cups of the stew, including some squash and broth, and blend until smooth. Return the blended mixture to the pot and stir to combine. This step creates the creamy base.
Stir in 1 tablespoon of the chopped sage. Taste and adjust salt and pepper if needed. Simmer uncovered for 5 more minutes.
Ladle into bowls and top with the remaining tablespoon of sage.