Advances in educational technology over the past 60 years present new opportunities for K-12 public school systems, opportunities to shift the focus from curriculum methods emulating the factories of the industrial age to curriculum methods embracing the connectedness of the information age, with the hope that teaching will be transformed from teacher-directed to student-centered, inquiry-based, collaborative learning opportunities. Many districts employ an individual in the role of technology coordinator to handle the technical and instructional support aspects necessary to lead and facilitate technology-driven learning initiatives. This qualitative study explored what two individuals at the district level in the state of Georgia actually do to leverage technology in ways that promote individualized and engaging instructional practices with the aim to better our understanding of how district level practices influence educational technology integration within teaching and learning and facilitate educational improvements. For this qualitative descriptive case study, two individuals identified at the district level as responsible for coordinating educational technology were purposefully selected. Data sources included three semi-structured face-to-face interviews, collected district level technology and curriculum policy and planning documents, and the researcher’s notes. An iterative and reflective process was employed to identify important categories and themes in the data from each case and then across cases. While it is not possible to statistically generalize the findings from this study, my findings suggest that: (1) the participating district level coordinators assume a leadership role resulting in support efforts particularly suited for transforming instructional practices in their particular system, (2) access to high-speed Internet and information technology remains a continual, ongoing obstacle to technology integration efforts, (3) instructional support provided for technology integration requires a perpetual, differentiated, and multilayered approach, and (4) a disconnect exists between the intended vision for educational technology integration and the actual focus of many educational initiatives and policies. Recommendations are provided for further research into the relationship between the leadership role of district level technology coordinators, the types of technology initiatives selected, the dimensions of technology integration support provided, and the governance structure of school systems.