While an X-as-a-service (XaaS) model has many benefits for vendors and customers alike, migrating from a traditional to an XaaS delivery model can wreak havoc on selling systems. When embarking on this journey, advance planning and preparation are critical. This report surfaces best practices gleaned from native and in-transition cloud companies and provides recommendations so that B2B marketing and sales leaders can avoid common pitfalls when migrating to XaaS.