Segment faces challenges in onboarding due to the complexity and variety of use cases it supports, which can overwhelm new users. To address this, Segment employs a use case-driven onboarding approach, starting with a survey to identify customers' specific needs and measure the value of their chosen use case to gain engineering buy-in. Segment uses machine learning-based adoption scores to track retention and success, relying on tools like Mixpanel to assess progress. They address onboarding challenges through targeted interventions and personalized communication, aiming to keep customers on a productive path. Segment designs onboarding experiences tailored to technical and non-technical personas, offering different strategies to engage users effectively. Despite experimenting with gamification, Segment focuses on delivering value-driven content and leveraging customer success managers (CSMs) for workshops and webinars to efficiently share expertise and best practices.