Heat olive oil in a large skillet over medium-high heat. Season beef with salt and pepper. Sear beef on all sides until browned.
Add onion, carrots, and celery to the skillet and sauté until softened.
Pour red wine into the skillet and scrape up any browned bits from the bottom of the pan. Simmer for 2-3 minutes.
Transfer beef and vegetables to the slow cooker.
Add beef broth, tomato paste, potatoes, thyme, rosemary, bay leaf, and Worcestershire sauce to the slow cooker. Season with salt and pepper.
Stir to combine. Cover and cook on low for 8-10 hours or on high for 4-5 hours, or until beef is fork-tender.
(Optional): In the last 30 minutes of cooking, whisk together 2 tablespoons of cornstarch with 2 tablespoons of cold water to make a slurry. Stir the slurry into the stew.
Remove bay leaf and herbs before serving. Serve hot.