Preheat the oven to 450 degrees . In a Dutch oven or large saucepan, heat the oil over medium-high. Add the onion and garlic and cook, stirring frequently, until golden, about 7 minutes. Add the carrots and the bell pepper; season with salt and pepper and cook, stirring, until softened, about 5 minutes. Add the corn, tomatoes, the ancho chile powder and 1 tbsp. of the oregano. Cook the chili, stirring frequently, until fragrant, about 2 minutes.
Add the beans, stock and 1 cup water; bring to a boil. Reduce the heat to medium and simmer until the liquid reduces slightly and the flavors meld, about 15 minutes. Transfer 3 cups of the chili to a blender, puree and return the mixture to the pot; season.
On a rimmed baking sheet, season the corn bread cubes and bake until browned in spots, about 5 minutes. Divide the chili among bowls; garnish with the corn bread croutons and the remaining oregano.