In the United States, young women continue to turn away from education that would prepare them for careers in the information technology (IT) workforce. Researchers studying this phenomenon have identified a wide range of contributing factors, including the career attitudes and guidance of family members, friends and mentors; curricular approaches to teaching software development skills; and well-entrenched stereotypes of IT professionals as anti-social "geeks." I describe a research project that explored a community-oriented approach to attracting and retaining women in our own College's IT education program. Our design goal was to seed and support the evolution of a multi-leveled emergent community pursuing its own developmental trajectory, with a focus on the online community for wConnect - a system that hosts a variety of online activities and communication options. In this talk, I will chronicle the system's development as an instance of action design research, showing how a sequence of four design phases were motivated by evolving design goals that led to systems with differing design rationales. I conclude with a synthesis and discussion of lessons learned, including design implications for online tools aimed at building and supporting developmental learning communities.