Disclosed herein are various embodiments for a vehicle listing generation and optimization system. An embodiment operates by receiving a request to generate a vehicle listing to sell a vehicle on a website. A plurality of vehicle listings similar to the vehicle to be sold are determined, the plurality of vehicle listings including a plurality of features providing information about a respective vehicle featured in the vehicle listing and a performance metric indicating an effectiveness of a respective listing. A first cluster of listings from the plurality of vehicle listings similar to the vehicle are identified based on based on performing artificial intelligence clustering with respect to the metric. Common features amongst a subset of the first cluster of listings are identified. A user interface of a sales template for selling the vehicle associated with the request via the website is generated, wherein the sales template includes the common identified features.