We analyze the evolutionary design of an online community system designed to support a developmental learning community of women: wConnect Online. The goal of this community is to engage, connect and support women at different developmental levels with respect to education and career goals in the computer and information sciences. We chronicle the system's development as an instance of action design research, showing how a sequence of four design phases were motivated by different design goals that led to systems with differing design rationales. After motivating the research program, we describe each design phase in detail, followed by a general synthesis and discussion of lessons learned.