Cut potatoes into large chunks. Place roast into crockpot, then add potatoes, broth, garlic powder, onion powder, Italian seasoning, salt, and pepper. Cover and cook on high for 6-8 hours.
Just before serving beef, preheat oven to 400 degrees. Cut asparagus into 2 inch pieces. Add to a bowl and stir in cherry tomatoes, shallots, thyme, salt and pepper. Bake for 5-6 minutes or until the asparagus is crisp-tender.
Serve beef with potatoes, asparagus, and oranges on the side.