Cloud-native reshaped software development by enabling scalability through containers and microservices. Today, AI is poised to drive an even more profound transformation in the tech landscape. This shift transcends technological advancements; it calls for a complete rethinking of software architecture and organizational collaboration. In this session, Pini Reznik will guide attendees through the evolution of software development, reflecting on the past, assessing the present, and looking to the future. First, we will revisit the transition from waterfall and monolithic architectures to agile cloud-native environments, drawing lessons from these past shifts. Next, we will examine how achieving cloud-native maturity sets the stage for a seamless AI-native transformation. Finally, we will explore the exciting potential and challenges of AI-native software development, considering the technologies and principles that will define this future. Key takeaways from the session include a deeper understanding of the forces driving software evolution, insights into the key requirements for an AI-native transformation, and a glimpse into the possibilities of AI-powered software development.