The off-shoring of telecommunications continues to expand achieving near to 70% compound annual growth over the last five years in the global off-shoring of business telephone services. Despite this significant success, selling business services or products over the telephone across culture presents challenges to telemarketers over and above those challenges conventional to mono-cultural business environments. Communicating with strangers across culture is challenging, particularly when the interlocutors do not share the same first language. When this exchange is limited to telecommunication mode, such obstacles may become inflated, yet little research-based literature exists on the topic. This paper reports on a case study of Filipino call-centre staff working in a multinational CRM company contacting Australian customers. Operational and management staff were engaged in a series of interviews over a period of several months and conversational analysis of phone calls was conducted in order to identify the key sociocultural and sociolinguistic challenges for telemarketers with culturally remote customers. This paper explored the extent to which cultural difference affected staff performance and customer satisfaction. Findings suggest that there is functional cultural alignment between Filipino staff and Australian customers and that cross-cultural training and cross cultural immersion in the target community can assist call centre staff cross the boundaries of language and identity with greater success.