Today’s In-Vehicle Information Systems (IVISs) are feature-rich systems that provide the driver with numerous options for entertainment, information, comfort, and commu- nication. Drivers can stream their favorite songs, read reviews of nearby restaurants, or change the ambient lighting to their liking. To do so, they interact with large center stack touchscreens that have become the main interface between the driver and IVISs. To interact with these systems, drivers must take their eyes off the road which can im- pair their driving performance. This makes IVIS evaluation critical not only to meet customer needs but also to ensure road safety. The growing number of features, the dis- traction caused by large touchscreens, and the impact of driving automation on driver behavior pose significant challenges for the design and evaluation of IVISs. Tradition- ally, IVISs are evaluated qualitatively or through small-scale user studies using driving simulators. However, these methods are not scalable to the growing number of features and the variety of driving scenarios that influence driver interaction behavior. We ar- gue that data-driven methods can be a viable solution to these challenges and can assist automotive User Experience (UX) experts in evaluating IVISs. Therefore, we need to understand how data-driven methods can facilitate the design and evaluation of IVISs, how large amounts of usage data need to be visualized, and how drivers allocate their visual attention when interacting with center stack touchscreens. In Part I, we present the results of two empirical studies and create a comprehensive understanding of the role that data-driven methods currently play in the automotive UX design process. We found that automotive UX experts face two main conflicts: First, results from qualitative or small-scale empirical studies are often not valued in the decision-making process. Second, UX experts often do not have access to customer data and lack the means and tools to analyze it appropriately. As a result, design decisions are often not user-centered and are based on subjective judgments rather than evidence-based customer insights. Our results show that automotive UX experts need data-driven methods that leverage large amounts of telematics data collected from customer vehicles. They need tools to help them visualize and analyze customer usage data and computational methods to automatically evaluate IVIS designs. In Part II, we present ICEBOAT, an interactive user behavior analysis tool for automotive user interfaces. ICEBOAT processes interaction data, driving data, and glance data, collected over-the-air from customer vehicles and visualizes it on different levels of granularity. Leveraging our multi-level user behavior analysis framework, it enables UX experts to effectively and efficiently evaluate driver interactions with touchscreen-based IVISs concerning performance and safety-related metrics. In Part III, we investigate drivers’ multitasking behavior and visual attention alloca- tion when interacting with center stack touchscreens while driving. We present the first naturalistic driving study to assess drivers’ tactical and operational self-regulation with center stack touchscreens. Our results show significant differences in drivers’ interaction and glance behavior in response to different levels of driving automation, vehicle speed, and road curvature. During automated driving, drivers perform more interactions per touchscreen sequence and increase the time spent looking at the center stack touchscreen. These results emphasize the importance of context-dependent driver distraction assess- ment of driver interactions with IVISs. Motivated by this we present a machine learning- based approach to predict and explain the visual demand of in-vehicle touchscreen inter- iii actions based on customer data. By predicting the visual demand of yet unseen touchscreen interactions, our method lays the foundation for automated data-driven evaluation of early-stage IVIS prototypes. The local and global explanations provide additional insights into how design artifacts and driving context affect drivers’ glance behavior. Overall, this thesis identifies current shortcomings in the evaluation of IVISs and proposes novel solutions based on visual analytics and statistical and computational modeling that generate insights into driver interaction behavior and assist UX experts in making user-centered design decisions.