The purpose of this study was to examine the influence of online collaborative learning experiences on students' digital collaboration skills and on the sustainability of e-collaboration in schools' culture--comparing individualistic versus collectivistic cultures. In addition, we explored how the leadership experience of schools' ICT coordinators was predicted by their sense of professionalism and cognitive, emotional and social aspects of perceived learning (PL), while leading the collaborative projects. The participants were ICT coordinators from 513 Israeli schools; 214 of whom were Hebrew-speakers, and 299 Arabic-speakers. The participants were asked to complete an online questionnaire, which included multiple-choice and open-ended questions. The results showed significant differences between a variety of the coordinator-related variables as a function of learning culture (more individualistic vs.more collectivistic). Coordinators' leadership experience was a powerful predictor of students' digital collaboration skills, but did not predict the sustainability of e-collaboration. Coordinators' emotional PL predicted the sustainability of collaboration in both schools with more individualistic and with more collectivistic learning cultures. The implications of the findings for educational theory and practise are discussed.