Fill large pot with water, add generous tablespoon of salt, and bring to rolling boil. Add cheese tortellini and cook according to package directions, typically 7-9 minutes. Drain well and immediately toss with drizzle of olive oil to prevent sticking. Set aside.

While pasta cooks, cut beef into bite-sized chunks about 1 to 1.5 inches across if not already cubed. Pat completely dry with paper towels. Season generously with salt and freshly cracked black pepper on all sides.

Heat large skillet over medium-high heat and add 3 tablespoons butter. When butter melts and foams, add crushed garlic. Let sizzle about 30 seconds until fragrant but not browned. Add beef chunks in single layer without crowding. Work in batches if needed.

Let beef cook undisturbed for 2-3 minutes until golden-brown crust forms on bottom. Flip each piece and cook another 2-3 minutes on second side for medium-rare to medium. Transfer cooked beef to plate, leaving garlic butter in skillet.

Reduce heat to medium and add remaining 2 tablespoons butter to skillet with garlic butter. Let melt completely. Pour in heavy cream and use wooden spoon to scrape up any browned bits from bottom of pan.

Bring cream to gentle bubble, then reduce heat slightly to maintain light simmer. Gradually sprinkle in grated Parmesan cheese while stirring constantly. Keep stirring for 5-7 minutes as cheese melts completely and sauce thickens to coat back of spoon. Sauce should be smooth and creamy. Taste and adjust seasoning with salt and pepper.

Add cooked tortellini to skillet with sauce. Gently fold them in using tongs or large spoon, making sure every piece gets coated. Let cook together about 1 minute so flavors meld and tortellini absorbs some sauce. Pasta should look glossy and luxurious.

Divide creamy tortellini among four plates or shallow bowls. Arrange beef chunks on top, distributing evenly. Drizzle any remaining sauce from skillet over top. Serve immediately.