Toast guajillos in a dry skillet 30–60 seconds until fragrant, then soak in hot water 15 minutes.
Blend soaked chilies, garlic, orange juice, vinegar, cumin, oregano, and 1/2 cup broth until smooth.
Season steak with 1 tsp salt. Heat oil in a large skillet over medium-high and brown steak in batches.
Return all steak to skillet, pour sauce and remaining broth over meat, cover, and simmer 45 minutes until tender.
Remove lid, increase heat, and cook 5–8 minutes to reduce sauce and crisp edges. Adjust salt.