Heat olive oil in a saucepan over medium-high heat.
Add ground beef and cook until browned, about 3-5 minutes, making sure to crumble the beef as it cooks; drain excess fat.
Stir in enchilada sauce, corn, chiles, 1/2 cup Monterey Jack cheese and 1/2 cup cheddar cheese; season with salt and pepper, to taste.
Place dip into a serving bowl, add remaining cheeses and microwave until cheese melts. Let cool 5 minutes before serving.
Preheat oven to 400 degrees F. Lightly oil two 10-ounce ramekins or coat with nonstick spray.
Divide the filling evenly into the ramekins and top with remaining cheeses.
Place into oven and bake until bubbly around the edges, about 5 minutes. Let cool 5 minutes before serving.