Most studies undertaken in the area of IT outsourcing seem to focus only on the customer’s perspective leaving a gap in knowledge about the vendor’s perspective. This study aims to correct this deficiency by investigating the views of four organisations providing IT services in Singapore, and comparing this to the current literature base of customer views. The findings showed that the vendor’s views about security, contract management and flexibility differed from the customer’s point of view. However, two issues, partnerships and vendor inexperience, seem to match the vendor issues found in this study. Additionally, two approaches were found to be used by vendors in the IT outsourcing activities, multiple-team approach and single-team approach. A multiple–team approach is likely to be used by vendors having a contract-based relationship and single-team approach is likely to be used by vendors having a partnership-based relationship.