Season the cubed beef with salt and pepper. Heat the olive oil in a Dutch oven or heavy pot over medium-high heat.
Add the beef in batches (to avoid overcrowding) and brown it on all sides, about 5–7 minutes per batch. Remove the browned meat and set it aside.
To the same pot, add the chopped onion, jalapeños, and garlic. Cook, stirring occasionally, until the veggies are softened, about 5-8 minutes.
Stir in the chili powder, cumin, paprika, and oregano.
Add the browned meat back to the pot, along with the diced tomatoes (with the juice) and broth. Stir to combine.
Bring the mixture to a boil, then reduce the heat to low. Cover the pot and let the chili simmer for 1 1/2–2 hours, stirring occasionally. The chili will thicken, and the flavors will deepen. If the sauce becomes too thick, add more broth as needed.
Serve the chili hot with your choice of garnishes: fresh cilantro, shredded cheese, sour cream, and/or diced onions. Pair it with cornbread or tortilla chips for a hearty meal.