School-driven technological innovation has the potential to positively impact on classroom practice, yet it can also be disrupted by incompatibilities between the existing school ecology and new educational technologies. To help mitigate this disruption a particular staff member often takes on a facilitative leadership role to champion new technology initiatives. However little is known about how this technology leader role impacts on the adoption of new technologies in the classroom. Taking a situated lens, we embarked on a multiple case study of four schools who were aiming to adopt a new literacy game in the classroom. Through interviews with technology leaders and fieldnotes from our site observations, we systematically analysed their actions and concerns over two academic terms. This highlighted an overwhelming concern with managing the material dimension of the technology, teacher agency and division of labour and mechanisms for communication and monitoring. Our findings raise important considerations for HCI researchers seeking to embed their technologies into practice alongside recommendations for supporting leaders tasked with coordinating this process.