Wearable medical devices, wireless sensor networks, and other energy-constrained sensing devices are often concerned with finding specific data within more-complex signals while maintaining low power consumption. Traditional analog-to-digital converters (ADCs) can capture the sensor information at a high resolution to enable a subsequent digital system to process for the desired data. However, traditional ADCs can be inefficient for applications that only require specific points of data. This work offers an alternative path to lower the energy expenditure in the quantization stage-asynchronous content-dependent sampling. This asynchronous sampling scheme is achieved by pairing a flexible analog front-end with an asynchronous successive-approximation ADC and a time-to-digital converter. The versatility and reprogrammability of this system allows a multitude of event-driven, asynchronous, or even purely data-driven quantization methods to be implemented for a variety of different applications. The system, fabricated in standard 0.5 µm and 0.35 µm processes, is demonstrated along with example applications with voice, EMG, and ECG signals.