When two Conservative synagogue preschools implemented the same two-year Judaic enrichment program, they experienced dramatically different outcomes - revealing how organizational culture shapes educational transformation. Despite high satisfaction among 42 participating teachers who attended biweekly Jewish studies classes, with three-quarters completing a culminating Israel trip, only Kehilat Israel preschool achieved significant organizational change and curriculum enhancement five months later, while Beth Jacob showed no measurable progress. Through qualitative methodology including pre- and post-program surveys, teacher evaluations, site visits, and semi-structured interviews, four critical factors emerged as essential for sustainable change: moral authority for decision-making, a culture of teamwork, a systems view of Jewish education, and commitment to ongoing Jewish learning. Data collection captured written evaluations at multiple program stages, informal site visit feedback, and post-trip surveys and journals. The stark contrast between schools, despite similar participation rates and positive personal experiences, illuminated how organizational capacity for change varies based on leadership stability, collaborative cultures, and integration of early childhood education within broader synagogue educational missions. These findings advance our understanding of the complex relationship between professional development and institutional transformation in Jewish educational settings.