The number of school districts needing to focus their attention on ensuring that their students are receiving a 21st Century education has grown considerably with the creation of the Smarter Balanced Assessment Consortium (SBAC) and the looming deadline of the 2014-2015 school year when the new assessments will be given. The assessment dates, along with the global demand for increased rigor and relevance also calls for a 21st Century schooling experience. In order to spearhead large scale reform, the superintendent of the school district must lead his/her school district to develop, implement, and sustain the changes made to address the 21st Century student. A mixed methods approach was used to answer four research questions related to the superintendent's implementation of 21st Century skills. Data was collected through an online survey with 35 responses with ten qualitative interviews of superintendents to support the four major findings. The first finding was that professional development and teacher training is essential to any district-wide reform. Without the proper training and support for teachers, its sustainable reform is unlikely. Next, the importance of teacher leadership shows that superintendents need to work with their principals to build a site-based school leadership team to effectively create a lasting reform. The third theme is that the superintendent must identify his/her essential stakeholders such as cabinet members, board members, community members, and principals in order to create support for the 21st Century skills transformation. Finally, the superintendent must hold his/her stakeholders accountable for the changes requested of them. Without accountability, it is difficult to sustain the 21st Century skills reform. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]