Regulated industries like banking and insurance are rapidly shifting to cloud-native technologies and platform engineering to enhance agility, scalability, and resilience. While this transformation offers new opportunities, it also presents considerable challenges, as it disrupts traditional workflows in favor of agile, DevOps-driven methodologies. Specifically, the adoption of DevOps fosters closer collaboration between previously siloed development and operations teams. Developers, in particular, face shifting expectations and mounting pressure due to accelerated release cycles, constantly evolving compliance mandates, and heightened demands for security and technical proficiency. These complexities can result in initial resistance toward agile practices and cloud technologies. To ensure a successful transformation, organizations must consider not only technical challenges but also cultural dimensions of change. This session explores how transparency in security and compliance fosters trust, addressing concerns and enabling developers to fully embrace agile workflows. Through a case study from the banking sector [anonymized], I showcase practical strategies to sustain momentum and navigate resistance effectively. By positioning trust as a catalyst for change, organizations in regulated industries—and beyond—can unlock the full potential of DevOps and cloud adoption, driving both cultural and technological transformation.