The medical transcription industry is rapidly evolving in terms of services and revenues for the last decade. This ITES contributed the largest employment growth rate in IT-BPO in 2013. The success of this industry was assisted by recent technology like Speech Recognition Technology (SRT). Because such technologies depend on people, there is a need to study on the experiences of the people behind those achievements. This paper addresses this gap by exploring Medical Transcriptionist’s (MTs) experiences using SRT. Findings revealed at least five themes prevalent to the experiences of MTs including audio file classification, valuable characteristics, negative observations, technostress coping, and highest quality orientation. This paper suggests that by looking at the experiences of MTs, current and future employers can gain insights in improving and enriching these outsourcing services. Furthermore, the presence of common themes indicates the possibility of performing a grounded theory based on substantive area of medical transcription.