While there is a substantial volume of information on digital transformation in companies and basic knowledge of the learning functions in organizations, there is little academic research on the skilling required of Learning and Development Practitioners or Professionals (LDPs) and the impact 21st century digital transformation has on their role. This mixed methods study shares lived experiences and the perceptions of LDPs and identifies challenges with which they are faced. Overall, the study explores transformation of LDPs within the construct of organizations and the digital evolution. The study reviews how LDPs are adapting to the rapid changes and the evolution of their learning environments, their input on the support they receive, and how adapting their skills and capabilities are crucial for future success. Furthermore, it identifies the changes that impact the Learning and Development function (L&D) and the effects on LDPs' roles, redefining and reimagining the purpose of organizational learning as it makes up the new ecosystem of learning driven by technology. It aimed to provide insights and answer questions on how LDPs are being supported by their leaders, are leaders removing roadblocks or adding new ones. The study used data, insights, and input from 56 learning practitioners currently impacted by agile organizational practices and the evolution of their role. Guiding the study were several key research questions which focused on the culture and support of learning by LDPs. Do LDPs feel they have opportunities to cultivate new skills and capabilities for the 21st century, and how have the adapted their practices to embrace digital learning. This study revealed 4 key conclusions related to creating a culture of learning for LDPs and providing an ecosystem which will contribute to their success and the broader community of practice. The study concluded with recommendations for future research and obtaining additional input of learning practitioners via interviews to seek out viewpoints which were not easily captured in surveys. Although additional points of view were welcomed, further recommendations identified excluding higher education practitioners to drive to more corporate organization results. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]