This book contains the refereed proceedings of the 5th International Conference on Software Business (ICSOB) held in Paphos, Cyprus, in June 2014. The theme of the event was "e;Shortening the Time to Market: From Short Cycle Times to Continuous Value Delivery."e;The 18 full papers, two short papers, two industrial papers, and two doctoral consortium abstracts accepted for ICSOB were selected from 45 submissions and are organized in sections on: strategic aspects, start-ups and software business, products and service business, software development, ecosystems, and platforms and enterprises.