Did you hear the one about Salesforce.com selling itself to a competitor? It's not a joke, at least according to news reports that sent shock waves through the technology world Wednesday.

The company that transformed CRM from an acronym to a ticker symbol on the New York Stock Exchange is toying with the idea of an acquisition Bloomberg reported. Specifically, reporters Alex Sherman and Cory Johnson noted Salesforce is apparently "working with financial advisers to help it field takeover offers after being approached by a potential acquirer."

While the potential suitor was not named, one thing is clear: the buyer would need extraordinarily deep pockets since Salesforce has a $49 billion market cap. That puts the spotlight on several companies, including Microsoft, SAP, IBM — and one especially close to the heart of Salesforce CEO Marc Benioff, Oracle.

And here's something else. Benioff has been steadily selling stock. In the past month, he's reduced his outstanding common shares from more than 37.937 million to 37.675 million yesterday, according to documents filed with the US Securities and Exchange Commission

Shares surged 13.5 percent in late trade yesterday on news of the rumored takeover.

Biggest Software Deal Ever

Benioff is a former Oracle executive and protégé of Oracle founder and CEO turned CTO Larry Ellison. Oracle has a market cap of about $194 billion.

But that's nothing compared to Microsoft's $396.87 billion market cap — and Benioff was an exceptionally happy tweeter about the Microsoft-Salesforce connection today, the first day of the Microsoft Build developers conference in San Francisco. Could his enthusiasm hint of a pending deeper connection?

While no one is claiming a sale is imminent, it does appear that Benioff and crew are taking the offer seriously and weighing strategic options. As Bloomberg noted, they are "working with bankers to field inquiries."

No wonder. Should the deal happen, it would easily be the largest acquisition of a software company in history.

Salesforce, by almost any measure, is the giant to be beat in the customer relationship management (CRM) in terms of sales and revenues as well as innovation and leadership. The top five CRM vendors accounted for 50 percent of CRM software revenue in 2013, according to Gartner's CRM Magic Quadrant report released last year. Salesforce continued to be the largest vendor overall in the CRM market with 16.1 percent of the market, Gartner noted.

But why would a guy like Benioff — arguably one of the most flamboyant, generous, larger-than-life personalities in the tech industry — agree to sell his baby? This is a guy who walks on coals and bungee jumps with motivational speaker Tony Robbins, who dines with international leaders and turns a big chunk of San Francisco into a sprawling celebrity-studded technology campus once a year for a little thing called Dreamforce.

Benioff founded Salesforce decades ago and almost single-handedly pushed the idea of cloud computing into the mainstream. The company has also led the way in other innovations in the CRM space, as Denis Pombriant of Beagle Research writes in a blog post.

Salesforce has a commanding lead in business software because while others were too timid to go after things like cloud, social, mobile, and IoT, Salesforce jumped in and made markets. Their future is full of all the new markets they’re going after and it ain't small."

So given all this, why would Benioff sell — to anyone?

Trading Big for Bigger?

Logically, the only thing better than heading a company like Salesforce would be heading something even bigger. That's why the idea of Salesforce joining Oracle must surely have some appeal, Rob Enderle of The Enderle Group said.

This is how he sees an acquisition playing out. "Marc would join Oracle as the heir in chief to Larry Ellison," he told CMSWire. "When Larry finally leaves Oracle for good, Marc would take command."

Daniel Ives, an analyst at FBR & Co. Capital, called a deal between Salesforce and Oracle a "golden combination" — and the most realistic pairing. In a research note, Ives explained that "Oracle is desperate to establish itself as a leader in the cloud, and acquiring the leading cloud company and bringing on board a visionary leader in Marc Benioff would help toward accomplishing this goal.”

And consider this: Just last month Ellison himself boasted that Oracle would "sell more cloud" than Salesforce this year. "I expect that might come as a big surprise to some of you. You won't have to wait very long to find out who's going to win this," he said during a quarterly conference call.

Could the secret to winning be an acquisition?

Oh Yea: The Customers

Last fall Benioff made a big deal out of Salesforce's shift from a sales-driven CRM company to one focused on long-term customer success. (Too bad about the CRM stock ticker, right?)

Benioff boasted at Dreamforce how Salesforce was launching a new analytics cloud to enable the company's evolution into a "customer success platform."

Benioff said there are now trillions of customer interactions that have created "an imperative of engagement, an imperative to connect." The challenge, he said, was that even though we have built billions of connected devices, customers remain disconnected from the marketers, salespeople and other employees of many companies.

"We know that if you connect, you engage deeply," he said. "Our vision at Salesforce is simple: it's to build that customer success platform."

More news on the potential deal could come within a few weeks: Salesforce announced yesterday that it will release its first quarter fiscal 2016 results on May 20 after the close of the market. The company will host a conference call at 5 PM EDT that day.

So how would an acquisition play out for the customers, much less their success? That's open to debate, especially if the buyer is Oracle.

After numerous acquisitions over the years Oracle can likely do an acquisition and tech integration in its sleep. Integrating Salesforce into Oracle's product stack will surely not be a problem, industry experts concur.

Screw 'Em?

But not so fast, Enderle told CMSWire. A sale to Oracle would be the worse case scenario for Salesforce's users, he said, adding bluntly: "Oracle has a reputation, frankly, for screwing its customers especially the customers that it acquired when it bought another company."

The best case scenario for Salesforce customers – other than no sale at all – would be an acquisition from a privately held Dell, he said. It's a longshot: Dell has a market cap of only about $24.19 billion.

But practicalities aside, "Dell would actually use its resources to improve Salesforce while leaving it alone to innovate," Enderle said. Still, he acknowledged that it is difficult to imagine that Dell could swing such a deal.

Then again, a few years ago it was hard to imagine that Michael Dell would have succeeded in taking Dell private. And before yesterday, it was almost unfathomable that Salesforce would even entertain the idea of a sale.

And remember one thing: Marc Benioff walks on hot coals. Who is to stop his next impossible move?

(CMSWire freelance writer Erika Morphy contributed to this story.)