This experience report explores the implementation of two specialized roles, Product Guardian and Security Master, within Alpha, a telecommunications solution provider. These roles were introduced to address challenges related to knowledge gaps, code quality, and security integration in Large Scale Agile (LSA) development. A qualitative case study was conducted with experienced LSA software professionals. The results highlight how Alpha cultivated a culture of continuous learning, team growth, and psychological safety, which proved instrumental in enhancing overall team outcomes. The report provides in-depth reflections on the role of leadership practices in fostering team autonomy, risk-taking, and double-loop learning, and it shares key lessons that offer practical insights for other organizations seeking to scale agile in complex, high-security projects. The report provides actionable recommendations for integrating security, fostering team collaboration, and managing complexity in LSA teams. These findings will be of interest to academics and practitioners seeking to optimize decisions and leadership strategies in LSA environments.