Preheat oven to 300 degrees F. Pat dry chuck roast. Season both sides with kosher salt and ground black pepper. In a large Dutch oven, heat olive oil over medium-high heat. Sear chuck roast on both sides until golden brown, about 5 minutes per side. Remove and set aside. Reduce heat to medium and melt butter in the same pot. Add sliced onions and cook for 25-30 minutes, stirring occasionally, until light brown. Add minced garlic and cook for 2 more minutes. Stir in white wine to deglaze, then let reduce by half. Sprinkle flour and stir to coat. Add beef broth, Worcestershire sauce, bay leaves, and herb sprigs. Bring to a simmer and season with salt and pepper. Return roast to the pot, cover 3/4 with liquid, and braise in oven for 3.5 hours until tender. Remove from oven and increase temperature to 400 degrees F. Shred beef, discard excess fat, bay leaves, and herb bundles. Top with shredded Gruyere cheese and return to oven until melted, 5-7 minutes. Serve warm with mashed potatoes or baguette slices.