This paper examines the leadership roles of distance learning administrators (DLAs) in light of the demand and need for value and quality in educational distance learning programs and schools. The author explores the development of distance learning using available and emerging technologies in relation to increased demand for education, training, skills, and certification in the global school economy of the 21st century. The paper brings to light the challenge that the value and quality debate poses as competition among colleges and universities increases and the labor market demands more talented knowledge workers in a space where competition affects professional prospects and graduate success. After examining the development and problems and challenges of distance education, the author looks at the critical leadership roles of distance learning administrators (DLAs) using ideals of leadership effectiveness as communicated by a survey of the literature. Using Mintzberg's theory of informational, interpersonal, and decisional managerial roles and activities, the author identifies the activities across which distance learning administrators could display exemplary leadership functions through sharing their vision, modeling the way, challenging the process, enabling others to act and encouraging and motivating the development and delivery of value and quality teaching and learning practices to capitalize on core and distinct competencies to build lasting competitive advantage. (Contains 3 tables.)