This dissertation was an in-depth investigation of successful online teaching in the context of higher education. It is presented in nontraditional dissertation format as approved by the Department of Curriculum and Instruction, Iowa State University. This dissertation includes three publishable journal articles that would represent Chapter 2, 3 and 4 of a traditional dissertation along with introduction and conclusion chapters. This dissertation argues that current standard-driven, technical, and one-size-fits-all approaches to preparing and supporting teachers for online teaching has been insufficient in addressing teachers' needs as they make a transition to online teaching and create a distinctive pedagogy for online learning. Because of these unstable patterns both at the organizational and faculty level, many online learning practices are employed as the replication of traditional classroom environments. Moreover, the research has been limited in terms of bringing teachers' voices into this process, which created a potential to regress them to passive roles. Therefore a critical review was conducted looking at the current literature on online teaching, and formulated a critique of the standards- and competency-driven vision of online teaching from the perspective of transformative learning theory. The study also provided an alternative perspective towards online teacher professional development considering teachers as adult learners, supporting teacher empowerment, promoting critical reflection, and integrating technology into pedagogical inquiry. Considering the importance of bringing teachers' voices to the discussion on online teaching, a multiple case study was conducted to investigate exemplary online teaching within different colleges of a university. Ethnographic interviews were conducted with six teachers who were selected through the nominations of online program coordinators in different colleges. The purpose was to look at the motivational factors that affected teachers' decisions to teach online, successful practices they employed to address the concerns and challenges related to their online teaching, and contextual and support factors that influenced the success of their online teaching. An analysis within each and across the six teacher interviews indicated that teachers reconstructed their teacher roles as they revisited their approaches to understanding the course content, designing and structuring the course, knowing their students, enhancing teacher-student relationships, guiding student learning, increasing teacher presence, conducting course evaluation, and creating an online teacher persona. Additional contextual factors impacted teachers' motivation for online teaching, such as their teaching history, students' profiles, institutional rewards, technology, and pedagogy support. Building on the results of the critical review and multiple case study, a third article additionally presents a framework that can be used as a guide to design, develop, and sustain online teacher support and professional development programs. This framework intends to recognize successful online teaching as the outcome of interaction among many factors at three levels--teaching, community, and organization. Together, these three articles address the issues in the current research and practice on online teaching and propose an alternative view on understanding, preparing, and supporting online teachers by focusing on transformation of teacher persona and empowerment of online teachers through reflective practices and pedagogical inquiry.