Smoky Chorizo Chili

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1 tablespoon extra-virgin olive oil

1 pound fresh chorizo, removed from casings 

Kosher salt and freshly ground black pepper 

1 medium red onion, chopped, plus more for topping 

1 small orange bell pepper, chopped 

1 small red bell pepper, chopped 

3 cloves garlic, chopped 

1 jalapeno, seeded if desired, chopped 

1 tablespoon ancho chile powder 

1 teaspoon ground cumin 

1 teaspoon smoked paprika 

1/2 teaspoon dried oregano 

Two 14.5-ounce cans fire roasted diced tomatoes 

2 cups low-sodium beef broth 

Two 15.5-ounce cans black beans, rinsed and drained 

1/2 small butternut squash, peeled and diced (about 2 cups) 

Parsley leaves, pickled jalapeno rings, grated Cheddar and sour cream, for topping