Providing secondary school students with early and ongoing exposure to experiences, information necessary to make informed decisions when selecting a career that connects to academic preparation and future aspirations has been left to career counsellors. However, not all schools are privileged to have them and even those who have them, these career counsellors also have other subjects to teach and this leaves them with limited time to attend to all the students or even plan for activities or forums on career guidance. This has denied secondary school students adequate career guidance that ought to help them relate their academics and extra curriculum activities to their career goals.This research provides a comprehensive study of the career guidance situation in the country and globally, the factors that ought to be considered for successful career guidance and the existing solutions. The collection of data was done using document reviews and questionnaires this was useful in identifying the improvements that need to be made in the way career guidance is done currently. Analysis of the data collected was done using Google analysis tool and the results used to come up with system requirements. Agile methodology was adopted as the software methodology for developing the application.The solution is a mobile application that can be introduced to students early enough to enhance their understanding of personality types and what different careers involve to help in career planning, development and guidance.This will be achieved by use of Holland’s intruments that is the Self Direct Search (SDS) and the Vocational Preference Inventory (VPI) to match students to career possiblities. A web based application was also developed to be used by professionals in offering guidance to students and for administrative purposes. Testing was carried by potential users of the application.