The introduction and application of IT(Information Technology) to a company has become to be viewed as a key factor for the business competitiveness and improved productivity. This study presents an approach to evaluation of a company's informatization level, which is especially appropriate for small and medium enterprises. The proposed evaluation method, based on the traditional questionnaire approaches, considers the various characteristics of the company, e.g., types of business, characteristics of customers, and locations of supply chains etc. A web-based system was developed to enable users to obtain the evaluation results from the evaluation method. The system also provides a function to produce valuable strategies for informatization by utilizing the case base which will be cumulated by repetitive evaluation requests. Finally, a real case was analyzed in order to verify the practicality of the evaluation system.