The purpose of the current qualitative case study was to explore which criteria administrators in a mid-sized public school district in Connecticut use when evaluating whether an online professional development program meets the needs of both the district and the teachers. The study also explored which criteria teachers use when they are selecting an online professional development program. The first research question was, what criteria do school administrators use in evaluating online professional development programs as effective professional development for teachers? The second research question was, what criteria do teachers use in selecting online professional development programs? Data were collected through interviews with administrators, interviews with teachers, and analysis of relevant documents. Participants in the study included district administrators who play a role in the approval process for professional development and district teachers who have completed online professional development. Several themes and subthemes for both administrators and teachers emerged. Administrators consider the structure, reputation, convenience, and district alignment when evaluating an online professional development program. Teachers consider the structure, topic, and convenience of online professional development when selecting a program. The primary suggestion for future research is an investigation into the reasons for the perception of teachers and administrators concerning the perceived discrepancy between how the two groups select effective professional development. Continued research may make the use of online professional development an increasingly productive means of professional growth. The findings of the current study may inform other public school districts of the value of such a collaborative effort.