For many years, organizations have been challenged with developing leaders. Organizational leaders understand the importance of developing new leaders that can carry the values, mission, and vision of the organization. They also know that those values are an important factor in achieving the organization's objectives. However, many leadership development efforts fall short from delivering the desired outcomes. The outcome is not because of a lack of resources or effort since organizations on average spend over $1252 per employee on training initiatives. This study was developed to help understand the perspectives of city leaders on online leadership training in a city located in Southern United States (Lacerenza, Reyes, Marlow, Joseph, & Salas, 2017). This new perspective provided meaningful insight which assisted in the development of a 7-step roadmap for an online leadership development program. Siemen's theoretical framework (Siemens, 2008), which presents connectivism as the foundation for learning in an increasingly digital world, was used as the theoretical foundation for this research. Using a qualitative descriptive case study design and email interviews, participants' feedback was gathered and applied to the creation of a roadmap that organizations can follow when developing an online leadership program. [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.]