Preheat the oven to 400ºF and place the poblano pepper and jalapeño pepper on a baking sheet. Drizzle on 3 teaspoons of olive oil and season with salt.
Then, trim the end of the garlic off opposite the root so the garlic cloves stay together. Place the garlic in a piece of tin foil and drizzle with 1 teaspoon of olive oil and season with salt. Wrap the garlic in the tin foil to seal. Place the garlic on the baking sheet with the peppers.
Bake the peppers and garlic at 400ºF for 20 minutes. Remove the peppers and let the garlic roast for an additional 10 minutes. Remove from the oven and set aside.
While the peppers are roasting, heat a large Dutch oven over medium/high heat and add the ground beef and break the meat up into small pieces. Season the beef with 1 teaspoon of salt and cook for 5 minutes.
Add the onion to the ground beef and cook the two ingredients together until the ground beef is fully cooked. Add the bell peppers and shishito peppers to the Dutch oven and toss all of the ingredients together. Remove the Dutch oven from the heat.
Next, place the roasted red peppers (and the liquid that is included in the jar) into a high-speed food processor along with the roasted poblano pepper and jalapeño pepper. Then, squeeze the softened roasted garlic cloves into the food processor and add ½ teaspoon salt.
Process the ingredients together until smooth and combined. Pour the roasted pepper sauce into the Dutch oven and place the Dutch oven back onto the heat. Add the chili powder, paprika, cumin, oregano, maple syrup, Worcestershire, beef broth, and the remaining salt to the dutch oven and mix all the ingredients together.
Bring the chili to a boil over high heat and then turn the heat to low and allow the chili to simmer for at least 20 minutes uncovered.
Serve the chili with a dollop of Greek yogurt or crema.