Sentry created an assistant widget, similar to Microsoft's Clippy, to improve user engagement and success with its product. The assistant is designed to be unobtrusive and guides users through key features, particularly for new users who need a gentle introduction. To make the assistant customizable and extensible, Sentry built a JSON-like specification system that allows developers to create new guides with ease. This system has been successful in increasing user engagement, measured by metrics such as the first-event rate, which saw a significant increase after implementing the assistant widget. The success of the assistant also led to improvements in guide iteration and scalability.