Heat olive oil in a large sauté pan over medium-high heat until shimmering but not smoking. Pat the chuck roast dry with paper towels and season liberally on all sides with kosher salt and freshly cracked black pepper, creating a flavorful crust during searing.

Once the roast is seared on all sides, transfer it to your slow cooker. In the same pan, reduce heat to medium without wiping out any bits left from the meat, add sliced onions with a pinch of salt and pepper, cooking until they soften, about 4 minutes.

To build layers of flavor, add smashed garlic cloves, tomato paste, brown sugar, Italian seasoning, garlic powder, onion powder, chili powder, along with more salt and pepper into the pan with onions; cook briefly until fragrant.

Pour Worcestershire sauce into the pan followed by a couple splashes of beef stock to deglaze it thoroughly; scrape up any browned bits from the bottom which contain concentrated flavors that will enhance your pot roast.

Transfer this onion-garlic mixture along with carrots and potatoes into your slow cooker where you’ve placed your roast; pour in remaining beef stock ensuring everything is submerged slightly while adding additional salt and pepper as needed.