An obstacle to developing a digital economy that appears virtually throughout the advanced economies is the question of effectively delivering digitalization efforts to small and medium-size enterprises (SMEs). These are, unlike their larger or smaller counterparts, confronted with conditions that often prohibit them from upgrading their business models by adapting advanced technologies. Large companies typically generate sufficient revenues that permit them to undergo advanced automatization and digitalization. For micro companies the digitalization process in itself is a relatively cheap endeavor as the majority build their business models on online platforms from the start. SMEs are large enough as to make the process of digitalization an expensive journey, yet too small to generate sufficient resources to embark upon it. Thus, countries have frequently attempted to establish supportive schemes that would provide SMEs with financial backing or opportunities to digitalize their businesses. The importance of such policies is essentially two-fold. First, SMEs in many cases constitute a bedrock for numerous economies. For instance, according to the European Union (EU) internal data from 2017 EU SMEs, excluding micro SMEs, account for 36% of total employment. Hence, making SMEs competitive is economically vital. Second, large companies, having a significant impact on the economy, are often directly dependent on hundreds of SMEs via the supply chain structures in place. Consequently, a large company, albeit digitalized itself, but dependent on non-digitalized suppliers will, in medium-to-long term, become considerably disadvantaged when facing similarly large companies based on a fully digitalized supply chain. Finding a process via which SMEs would be digitalized effectively has, therefore, become an ultimate goal for both the public authorities and private sector itself. This research selected several sample countries in Central and Eastern Europe, namely Germany, Austria, the Czech Republic, and Slovakia, in order to compare and contrast economic viability and the effectiveness of varying programs and initiatives from both public and private spheres. Specifically, this paper conducted qualitative analysis of automatization and digitalization implications varying programs have had on a few (1 to 3) selected SMEs companies per sample country (to be included SMEs had to match pre-determined criteria, especially regarding employee base, and SME’s sector orientation–ideally manufacturing, engineering, and logistics) in order to determine the effectiveness of programs under scrutiny and best practices that should be followed. Likewise, it generated data demonstrating what type of cooperation and funding scheme, public/private/public-private has proven most effective.