In this paper, we design and implement a deep advertising signage system, called DeepAd, with context-aware advertisement and cyber-physical interaction based on Internet of Things (IoT) technologies. In the DeepAd system, instant sensing and diverse interacting features are integrated with an IoT signage, which can (1) transmit multimedia contents and receive specific messages to/from smartphone users, (2) sense and interact with nearby individuals through image sensors, (3) embed context-aware advertisement information in sound waves, and (4) customize the on-screen 3D doll with an audience's face on demand. Through built-in sensors and smartphone interfaces, DeepAd can interact with nearby audiences via real-time multimedia services on the IoT signage in a click-and-drag manner. In addition, DeepAd investigates data-over-sound techniques to send embedded status-related advertisement via background music/voice. Furthermore, DeepAd explores deep learning based face changing and recognition to provide innovative and customized services to smartphone users. This paper demonstrates our current prototype consisting of the Android App, advertising server, and IoT signage.