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Discover how Volkswagen navigated the complex landscape of IT automation in a highly regulated industry. Learn about the challenges and solutions in modernizing legacy systems, ensuring reliability, and implementing automation across the entire stack from bare metal to databases. Explore the journey of a large international company balancing strict policies, long-term production requirements, and the need for future-ready infrastructure. Gain insights into the process of building an effective team, interviewing customers, and managing costs while achieving modernization objectives. This conference talk provides valuable lessons and real-world experiences for professionals seeking to enhance automation in complex organizational environments.