Preheat the oven to 350°. Season the steak with salt and pepper. In a large nonstick skillet, heat 1 tablespoon of the olive oil over medium-high heat. Add the steak and cook until browned, 4 minutes on each side. Transfer to a cutting board and let cool; cut into thin strips.

In the same skillet, heat 1 more tablespoon olive oil over medium heat. Add the onion and cook, stirring occasionally, until softened, about 4 minutes. Stir in the tomatoes and their juice, the garlic, chipotle and cumin and cook over medium-high heat, stirring, until the mixture thickens, about 3 minutes; stir in the sliced beef and chopped cilantro.

Heat a grill pan or griddle over medium heat. Brush one side of each tortilla with the remaining 1 tablespoon olive oil. Working in batches, cook the tortillas oiled side down until lightly browned, 1 to 2 minutes.

Arrange 4 tortillas grilled side down on a baking sheet. Divide the steak mixture among the tortillas and sprinkle with the cheese. Top with the remaining tortillas, grilled side up. Bake until the cheese is melted, about 10 minutes. Cut into wedges and top with the cilantro leaves.