This paper aims to discuss the pilot study and analysis of the current development and measurement practices in Jordanian small software firms. It is conducted because most developers build web applications without using any specific development method and don't know how to integrate the suitable measurements inside the process to improve and reduce defect, time and rework of the development life cycle. Furthermore the objectives of this pilot study are firstly; determine the real characteristics of small software firms in Jordan. Secondly, investigate the current development and measurement practices. Thirdly, examine the need of new development methodology for building web application in small software firms. Consequently, Pilot survey was conducted in Jordanian small software firms. Descriptive statistics analysis was used to rank the development and measurements methods according to their importance. This paper presents the data, analysis and finding based on pilot survey. These actual findings of this survey will contribute to build new methodology for developing web applications in small software firms taking to account how to integrate the suitable measurement program to the whole development process and also will provide useful information to those who are doing research in the same area.