The world is constantly changing creating a new environment. One of the main factors in this process is the Digital Transformation which requires adjustment of skills, institutions, processes and business models. The European Commission started to cope with this topic in last twenty years and today their activities are according to the “Europe 2020 Strategy.” Enhancement of digital skills is one of the priority. Serbia also makes an effort in this area and policymakers already adopted several documents and policies. The main issue is a lack of scientific research that cover the subject – ex ante and ex-post analysis of adopted policies. We consider this subject very important having in mind that the digital skills become one of the basic element for the national growth and competitiveness. This paper presents findings on the existing level of digital skills of the workforce in Serbia, with focus on the gender gap. Findings are based on a standardized survey conducted during September 2017, within the pilot study research. Results show that the level of digital skills is Serbia is lagging behind the EU average and that the level of digital skills of Serbian women is lower than men.