With the rise of modern digital connectivity technologies, Digital Transformation (DT) is now an issue for most companies across almost all industries. DT is an evolution to digitalizing internal processes, offering digital services and products, and improving the customer experience. Prior studies have explored different barriers that hinder successful DT. Our study follows a quantitative design to explore further how these barriers are perceived by staff at small and medium-sized enterprises (SMEs) compared to larger enterprises (LEs). Our sample comprises participants from 189 SMEs and 221 LEs. In general, results indicate a somewhat similar perception of their DT processes. In detail, setting up new positions to manage DT poses a more intense barrier for SMEs.