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In a large pot over medium heat, heat oil. Add onion, carrots, garlic, tomatoes, salt, pepper, oregano, and red pepper flakes (if using) and cook, stirring occasionally, until vegetables soften, 6 to 8 minutes. Add rice and stir until toasted, about 2 minutes.
Add 2 cups broth and bring to a simmer, stirring occasionally. Cover, reduce heat to medium-low, and let cook until rice is al dente, 30 to 35 minutes.
Return heat to medium and add beans and remaining broth. Stir to combine and continue cooking until slightly thickened and rice is completely tender, 12 to 15 minutes more. Remove from heat and stir in pesto.
Garnish with Parmesan, pine nuts, and herbs before serving.