Heat olive oil in a large Dutch oven over medium-high heat. Season beef cubes with salt and pepper, then brown on all sides, about 6-8 minutes total. Remove beef and set aside.
In the same pot, add diced onion and cook until softened, about 5 minutes. Add minced garlic and cook for 1 minute until fragrant.
Pour in red wine to deglaze the pot, scraping up any browned bits from the bottom. Let it simmer for 2-3 minutes to reduce slightly.
Return the beef to the pot and add beef broth, diced tomatoes, tomato paste, basil, and oregano. Bring to a boil, then reduce heat to low, cover, and simmer for 1.5 to 2 hours until beef is very tender and shreds easily.
While the beef is braising, cook tortelloni according to package directions. Drain and set aside.
Once beef is tender, use two forks to shred it directly in the sauce. Stir in heavy cream and let it simmer for 5 more minutes.
Add the cooked tortelloni to the sauce and gently toss to coat. Cook for 2-3 minutes until heated through.
Serve immediately, garnished with fresh parsley and grated Parmesan cheese.