This chapter will present the early unfolding of a cross-organizational Community of Practice (CoP) for heads of school of 14 independent Jewish day schools in the Boston area. Member schools are diverse in terms of the grade levels served, age and size of school, organizational structure and the market segments served within the Jewish population (e.g. Reform, Pluralistic, Orthodox). The chapter will articulate the challenges faced by the community facilitators to a) help school leaders overcome the initial barriers to engagement; b) meet the diverse needs of members; and c) engage heads in system-wide and individual school improvement. It will identify the strategies used by facilitators to overcome these challenges and help the heads of school develop a shared sense of identity and purpose. The emergence of a subgroup of Orthodox schools will be examined in relation to the larger CoP. Member testimonials, attendance data and recounting of community events and activities will demonstrate the accomplishments of the Heads of School CoP during its first year of activities. Finally, the chapter will look at the lessons learned by facilitators and discuss potential future challenges and strategies.