Strategic Information Systems Planning (SISP) is a process to make organisation implement IS/IT infrastructure in align with strategic plan of the organisation. This is one of the major issues found in current Information Systems therefore proper planning is required to solve the matter. Most of the organisation want to produce valuable software in short time period, and reduce the cost. Different software development methodology in practice has been identified and agile has been selected. This research is conducted taking a success and failure examples in implementing agile methodology (scrum). Analysis tools in this research are NIMSAD and DESMET as a strategic information system framework. Results of analysing, bring information and comparison about the failure and success factors while implementing agile methodology (scrum) in Spotify and Healthcare.gov and alignment of Business and IT were analyse using strategic alignment model (SAM). This paper presents a future direction towards software development methodology in IT Projects.