Return on Investment or ROI is one of the most clichéd and paradoxical evaluation metrics used in any purchasing decision. Paradoxical as it is frequently impossible to gauge the eventual potential improvements from capital investments. However, it doesn’t stop anyone from trying and does help to guide tech stack decisions, and as flawed as it is, without it, you are buying in the dark. The purchasing process of new software has become so muddled with exorbitant costs, exhausting timelines and conspicuous agendas. COVID-19 has certainly sped up digital transformation, and leaders are realizing that getting through this crisis involves innovation, however In many cases, CIOs and tech departments would rather trundle along with outdated systems rather than engage the sales cycle. Developments within the software industry are streamlining processes and saving companies millions. If the buying process managed to get out of its own way and fulfill customer needs easily, the buyer’s organization could be dramatically more profitable and efficient.