Salesforce has built a deep bench of executive talent via acquisition

When Salesforce acquired Quip in 2016 for $750 million, it gained CEO and co-founder Bret Taylor as part of the deal. Taylor has since risen quickly through the ranks of the software giant to become president and COO, second in command behind CEO Marc Benioff. Taylor's experience shows that startup founders can sometimes play a key role in the companies that acquire them.

Benioff, 56, has been running Salesforce since its founding more than 20 years ago. While he hasn't given any public hints that he intends to leave anytime soon, if he wanted to step back from the day-to-day running of the company or even job share the role, he has a deep bench of executive talent including many experienced CEOs, who like Taylor came to the company via acquisition.

One way to step back from the enormous responsibility of running Salesforce would be by sharing the role.

He and his wife Lynne have been active in charitable giving and in 2016 signed The Giving Pledge, an initiative from the The Bill and Melinda Gates Foundation, to give a majority of their wealth to philanthropy. One could see him wanting to put more time into pursuing these charitable endeavors just as Gates did 20 years ago. As a means of comparison, Gates founded Microsoft in 1975 and stayed for 25 years until he left in 2000 to run his charitable foundation full time.

Even if this remains purely speculative for the moment, there is a group of people behind him with deep industry experience, who could be well-suited to take over should the time ever come.

Resurrecting the co-CEO role

One way to step back from the enormous responsibility of running Salesforce would be by sharing the role. In fact, for more than a year starting in 2018, Benioff actually shared the top job with Keith Block until his departure last year. When they worked together, the arrangement seemed to work out just fine with Block dealing with many larger customers and helping the software giant reach its $20 billion revenue goal.

Before Block became co-CEO, he had a myriad other high-level titles including co-chairman, president and COO - two of which, by the way, Taylor has today. That was a lot of responsibility for one person inside a company the size of Salesforce, but promoting him to co-CEO from COO gave the company a way to reward his hard work and help keep him from jumping ship (he eventually did anyway).

As Holger Mueller, an analyst at Constellation Research points out, the co-CEO concept has worked out well at major enterprise companies that have tried it in the past, and it helped with continuity. Salesforce, SAP and Oracle all didn't miss a beat really with the co-CEO departures," he said.

If Benioff wanted to go back to the shared responsibility model and take some work off his plate, making Taylor (or someone else) co-CEO would be one way to achieve that. Certainly, Brent Leary, lead analyst at CRM Essentials sees Taylor gaining increasing responsibility as time goes along, giving credence to the idea.

Ever since Quip was acquired Taylor seemed to be on the fast track, becoming president and chief product officer less than a year-and-a-half after the acquisition, and then two years later being promoted to chief operating officer," Leary said.

Who else could be in line?

While Taylor isn't the only person who could step into Benioff's shoes, he looks like he has the best shot at the moment, especially in light of the $27.7 billion Slack deal he helped deliver earlier this month.

Taylor being publicly praised by Benioff for playing a significant role in the Slack acquisition, Salesforce's largest acquisition to date, shows how much he has solidified his place at the highest levels of influence and decision-making in the organization," Leary pointed out.

But Mueller posits that his rapid promotions could also show something might be lacking with internal options, especially around product. Taylor is a great, smart guy, but his rise shows more the product organization bench depth challenges that Salesforce has," he said.