Cut beef into 1-inch cubes. Pat dry thoroughly, then season with 1 ½ teaspoon Kosher salt, 1 teaspoon ground black pepper, and a few drizzles of olive oil.
Heat a few drizzles of oil in a large 6-quart Dutch oven over medium-high heat. Sear the beef until caramelized and golden brown. It's important to sear in batches in order to not overcrowd the pot, otherwise it will steam and not brown. Remove from the pot and set aside. Tip: The beef may release moisture, absorb it with paper towel to encourage better browning.
Reduce heat to medium, then add more olive oil. Add the onions and cook for about 5 minutes until softened. Then, stir in minced garlic and thyme for another 1-2 minutes until fragrant.
Add the tomato paste, stirring to coat. Then, stir in balsamic vinegar and maple syrup.
Next, add the red wine and simmer about 2 minutes. Then add beef broth and bring back to a low simmer.
In a bowl, dissolve ¼ cup flour with ½ cup room temp water to make a slurry. Stir in the slurry into the pot. It will thicken as it simmers.
Return the seared beef into the pot, along with bay leaves an rosemary. Season with salt and pepper to taste. Bring back to a low simmer. Cover and cook over low heat on the stovetop for 1 hour, stirring occasionally.
Next, add butternut squash and continue cooking, covered, for another 30 minutes until tender.
To serve, garnish with chopped parsley. Serve with bread or your favorite sides, and enjoy!