What is the future of the conventional phone-based corporate sales teams? As consumers grow more and more accustomed to purchasing online everything from holiday gifts to weekly groceries to boats and homes, companies have better and better opportunities to automate their own corporate sales processes. Today's companies are encountering an era of accessible and scalable information technologies (IT) and of an increasingly e-commerce-savvy customer base. This paper explores a decision process in a case company using analytical hierarchy process (AHP). Decision profiled in this study is to determine the most viable decision between developing an automated custom sales order interface system and using the existing manual process in which customers contact sales teams to place orders. Decision model is based on multiple criteria in order to assess each candidate system risks and benefits. Study analyzes the current trend of IT integration throughout the supply chain, develops a decision model based on user interviews, and aims to determine the circumstances under which automating the process is the best choice. Results indicate that, importance of decision criteria differs with respect to duration of contracts each customer makes. For instance, development cost has been identified as the most heavily weighted decision criterion at six month long contract cases whereas all decision criteria which are data quality, development costs, organizational politics and customer experience are weighted equally at one year contract cases. Results have also shown that although organizational politics has been ranked relatively lower in six months and one year contract cases it takes considerable precedence at contracts with duration of two years and more.