A system may use optical character recognition (“OCR”) techniques to identify license plates or other textual information associated with vehicles. Based on this OCR information, the system may determine additional information, such as users associated with the vehicles. The system may further obtain other information, such as history information associated with the vehicles and/or the users (e.g., via an “opt-in” data collection service). Ad content may be selected based on trends associated with the users and/or vehicles, and may be presented via “smart” billboards (e.g., billboards that may dynamically display different content).