In a large Dutch oven or heavy pot over medium heat, heat oil. Add beef and cook, turning occasionally, until seared on all sides, about 10 minutes. Transfer beef to a plate.

Coat bottom of pot with oil if needed and heat over medium-high heat. Cook onion, carrots, and celery, stirring occasionally, until softened, about 7 minutes; season with salt and pepper. Add garlic and tomato paste and cook, stirring, until garlic is fragrant and tomato paste is darkened, about 2 minutes. Return beef and any accumulated juices to pot. Add broth, wine, Worcestershire, thyme, and bay leaves. Bring to a boil, then reduce heat to medium-low and bring to a simmer; season with salt and pepper. Cover and simmer, stirring occasionally, until beef is tender, 30 to 45 minutes.

Add potatoes and simmer, covered, until potatoes are tender, about 15 minutes.