Heat the olive oil in a skillet over medium heat. Add the beef cubes and brown them on all sides for a few minutes.
Transfer the browned beef to the slow cooker.
Add the butternut squash, carrots, onion, and garlic to the slow cooker.
Stir in the tomato paste, Italian seasoning, salt, and black pepper.
Pour the beef broth over the ingredients and stir gently to combine.
Cover and cook on low for 8 hours until the beef is tender and the vegetables are soft.