Bring salted water to a boil. Add cheese ravioli and cook—3–4 minutes for fresh or 6–8 for frozen—until tender. Drain and set aside.
Heat olive oil and butter in a large skillet over medium-high heat. Add sliced steak, season with Cajun spice, smoked paprika, salt, and pepper. Sear for 2–3 minutes per side until browned and crisped. Transfer to a plate.
Lower heat to medium. In the same skillet, melt butter, add garlic, and sauté for 30 seconds until fragrant.
Stir in heavy cream and broth. Simmer gently, then mix in Parmesan, Italian seasoning, red pepper flakes, salt, and pepper. Cook 2–3 minutes, stirring until smooth and slightly thickened.
Add cooked ravioli to the skillet and toss in the sauce. Return steak to the pan and spoon sauce over. Simmer for 2 minutes to heat everything evenly.
Garnish with fresh parsley and extra Parmesan. Serve warm directly from the skillet or plated individually.