This case provides principal licensure candidates a strategic perspective on leading and managing educational technology initiatives. It presents issues related to vision setting, planning, implementation, organizational structure, and decision making. The case narrative is presented from the perspective of a principal, but it can also be used to prompt reflection from the perspective of a central office administrator such as a superintendent, assistant superintendent, technology director, or professional development coordinator. The case includes a preliminary knowledge-building activity and discussion questions, which, combined, prepare administrators to exercise technology leadership for school improvement through environmental scanning, organizational analysis, and performance measurement.