Heat oil in large pot over medium-high heat. Add onion and cook, stirring often, until it starts to brown (~5 min). Reduce heat to medium. Add carrot and continue cooking, stirring often, until the vegetables are soft (~4-5 more min).
Add garlic and continue to cook for an additional minute.
Next, stir in broth and bring to a boil over high heat. Add squash, tomatoes, beans, chili powder, cumin, cinnamon, salt, and cayenne. Cover and return to a boil.
Reduce heat to maintain a gentle simmer and cook, uncovered, until the squash is tender, about 30 minutes.