In 5-quart Dutch oven, heat oil over medium heat. Cook onion and garlic in oil until onion is tender. Add tomatoes and broth, breaking up tomatoes. Heat to boiling; reduce heat. Cover; simmer 15 minutes, stirring occasionally. Stir in pesto, whipping cream, salt and pepper with whisk until blended. Remove from heat. Cool 10 minutes. In blender, place half of soup. Cover; blend on high speed until smooth. Return to Dutch oven. Repeat with remaining soup.