This chapter presents a discussion on the challenges associated with managing and gaining insights from the massive amount of behavioral data available to digital service providers. The case studies presented demonstrate the potential benefits of leveraging AI tools to automate the analysis process and gain valuable insights into user behavior at scale. The use of algorithmic analysis can identify malfunctioning features or common interaction pathways leading to negative outcomes, and exploratory analyses can uncover unexpected use cases that may unlock new markets or revenue streams. The chapter concludes that AI-enabled insight is becoming increasingly critical to successful PLG strategies as it enables businesses to better understand their users and make data-driven decisions that support growth and improve the user experience. The examples presented here suggest that there are still many possibilities for deriving insights from user behavior data that have not yet been explored.