This article presents an interview with Ken Udas, chief executive officer of UMassOnline. During the past decade, Udas has held leadership positions in online university initiatives and has served the field through his leadership in organizations including the Association of Public Land Grant Universities, EDUCAUSE, IMS, Sloan-C, and the American Distance Education Consortium. Prior to joining UMassOnline in September 2009, Udas was executive director of Penn State World Campus; director of SUNY Learning Network, The State of New York Systems Administration; E-Learning director at The Open Polytechnic of New Zealand; and director, Distance Learning Network (DLN), EdNet, CARANA Corporation USAID Project based in Almaty, Kazakhstan. In the interview, Udas shares what he has learned from having had leadership positions in the large systemwide implementations of online distance learning. As an experienced advocate for openness--open source software (OSS) and open educational resources (OER), Udas explains what openness offers to distance education.