Amidst the global digital transformation and the expanding IT sector, particularly in Ukraine, it is essential to examine how digitalization affects structural shifts within the national economy. This study aims to analyze the impact of digitalization on the growth of Ukraine’s IT sector, focusing on comparing the economic metrics of freelancing and outsourcing and providing strategic recommendations to enhance entrepreneurial activity in this area. During the research, the methods of expert evaluations, economic-mathematical modelling, comparative analysis, and statistical data analysis were used. The research revealed that digitalization significantly influences structural changes in the national economy, particularly through the advancement of the IT sector. It was established that outsourcing has significant advantages compared to freelancing in terms of such indicators as the share of the GDP of the IT sector and the volume of exports of IT services. By analyzing the economic indicators of freelancing and outsourcing, specific recommendations were developed for the continued growth of Ukraine’s IT sector, aimed at boosting entrepreneurial activity and creating new job opportunities. The key factors influencing IT specialists’ employment choices were summarized, which is crucial for the continued development of the national economy in the context of digitalization. The practical value of this research is that its findings can be utilized to enhance Ukraine’s IT sector, particularly by backing outsourcing businesses and promoting the expansion of freelance platforms.