Product software export can be an attractive option for small and medium sized IT-companies operating in small local markets. In practice however, little support is offered for specifically those type of companies to support strategic preparation and to enable thorough export planning. The central aim of this paper is to present a Product Software Export Planning Method (PSEPM) that supports the decision making of management of product software companies to enter foreign markets. The method builds upon existing insights from the success factors of software export and strategic planning. It facilitates systematic export planning through strategic country analysis, i.e. a systematic comparison between the companies’ home country and the export country of interest. A similarities/differences and opportunities/ threats (SDOT) analysis is the other key part of the method. Through the identification of opportunities and threats, the specific challenges of entering the foreign market can be identified. The method has been applied to a case study at a Dutch product software company specialized in workforce planning applications. In addition, an expert validation was conducted by interviewing (former) board members of IT-companies. The method turned out to be useful for supporting export planning of small and medium size product software companies.