As of the most recent quarter, Oracle had about $51 billion in cash, which is good because Salesforce isn't cheap. Its shares trade around $82, up 4% for the year to date compared with a 1.2% rise in the S&P 500. It has a market cap and enterprise value of around $55 billion through Monday's closing price. But buying Salesforce would bring Oracle $2 billion in cash.
Both companies offer enterprise software for sales and other functions, and Oracle is racing to catch Salesforce in with its subscription-based software. At the same time, both companies would complement each other's weakness.
For instance, for all of Salesforce's cloud prowess, the company has run out of ideas. Salesforce has saturated its own market and has had limited success growing further in the enterprise IT space. While Oracle has done a solid job in catching up to Salesforce in the cloud, it will always remain on the hunt, never the hunted.
Microsoft, though it still trails Salesforce in the realm of customer relationship management, is about to widen its lead on Oracle. So Oracle and Salesforce can benefit from a merger. The only question is how much would it take to close a deal.