Start by heating 1 tablespoon of olive oil in a large pot over medium-high heat. Add chicken and sausage, cooking until the chicken is done and the sausage is browned, about 5-7 minutes. Remove from the pot and set aside.
In the same pot, add the remaining olive oil along with the bell peppers, celery, jalapeño, onion, and garlic. Cook until the onions are soft, about 6 minutes.
Mix in the crushed tomatoes, chicken stock, rice, Cajun seasoning, thyme, cayenne, and bay leaf. Bring to a simmer then lower the heat, cover, and let it cook until the rice is almost done, about 25-30 minutes. Stir occasionally to prevent sticking.
Add the shrimp and okra to the pot, stirring until the shrimp turn pink and are cooked through. Return the chicken and sausage to the pot, remove the bay leaf, and get ready to serve.
Season the jambalaya with salt and pepper, and more Cajun seasoning if you like. Once seasoned to your taste, it's ready to enjoy.
Serve the jambalaya hot with your choice of garnishes, or store it in the fridge for up to 3 days.