By Trey Thoelcke
Publication Date: 2026-03-12 14:20:00
Ten years ago, Oracle (NYSE:ORCL) and Salesforce (NYSE:CRM) both experienced a crucial shift: legacy software companies struggled to reinvent themselves as cloud companies. Both made it, but the paths diverged greatly, as did the returns.
Oracle spent much of the late 2010s migrating its massive installed base to the cloud. The real acceleration came later, when demand for artificial intelligence (AI) infrastructure exploded. Oracle’s cloud data centers became key locations for AI training workloads, and the company found itself in an exceptional pipeline. Remaining performance obligations reached $553 billion in the third quarter of fiscal 2026, up 325% year-over-year, suggesting that contracted revenue has already been on the books for years.
Salesforce dominated customer relationship management (CRM) and aggressively expanded into marketing, analytics, and collaboration. The growth was real, but the stock significantly outperformed fundamentals during the 2020-2021 boom and has been in a correction phase since then. Salesforce is down…
