This chapter applies Cultural-Historical Activity Theory (CHAT) in order to explore the complexities of pedagogical leadership within Singapore’s commercialised early childhood education and care ECEC environment, an environment which in Singapore’s early childhood care and education sector is in its nascent phases of development as it moves towards becoming a knowledge-based profession. The authors present findings from a study of principals and directors of early childhood settings who consider ways in which pedagogical leadership could be enacted within a marketised educational system. The study reveals that pedagogical concerns should be central to an educational leader’s work, but oftentimes, leaders are pulled in many different directions towards managerial and administrative tasks. There appears to be a struggle between two conflicting motives: engaging in pedagogical work and/or performing administrative tasks.