The 2016 acquisition of Quip by Salesforce for $750 million included Bret Taylor, Quip’s CEO and co-founder, in the agreement. Taylor has since experienced a rapid advancement within the software company, ultimately becoming president and COO, positioned as the second-highest executive after CEO Marc Benioff. Taylor’s career trajectory demonstrates that founders of acquired startups can frequently assume significant leadership positions within the acquiring organization.

Marc Benioff, age 56, has led Salesforce since its inception over two decades ago. Although he has not publicly indicated any plans for departure, should he choose to reduce his involvement in the company’s daily operations or explore a co-leadership arrangement, he has a strong team of executive leaders available. This group includes numerous seasoned CEOs, many of whom, like Taylor, joined Salesforce through acquisitions.

Benioff and his wife, Lynne, are known for their philanthropic contributions and, in 2016, joined The Giving Pledge—an initiative established by The Bill and Melinda Gates Foundation—committing to donate the majority of their fortune to charitable causes. It is conceivable that he might dedicate increased time to these philanthropic pursuits, mirroring the path taken by Gates two decades prior. For context, Gates established Microsoft in 1975 and remained for 25 years before transitioning in 2000 to focus entirely on his charitable foundation.

While this possibility is currently only a consideration, a team of highly experienced individuals stands ready to potentially assume leadership roles should the need arise.

Revisiting the Co-CEO Structure

A potential approach for lessening the extensive demands of leading Salesforce involves a shared leadership model. Notably, Benioff previously operated with a co-CEO, Keith Block, for over a year beginning in 2018, until Block’s resignation the previous year. During their collaboration, the arrangement proved successful, with Block focusing on key, large-scale clients and contributing to the company’s achievement of a $20 billion revenue target.

Prior to assuming the co-CEO position, Block held several other significant executive roles, including co-chairman and president & COO – positions Taylor currently holds, in part. Managing such a broad scope of duties within an organization as large as Salesforce presented a considerable undertaking; however, elevating him to co-CEO from COO served as recognition for his contributions and aimed to retain his services (though he ultimately left the company).

According to Holger Mueller, an industry analyst at Constellation Research, the co-CEO model has demonstrated effectiveness in other prominent enterprise organizations, facilitating a smooth transition of leadership. “Companies like Salesforce, SAP, and Oracle successfully navigated co-CEO transitions without disruption,” he observed.

Should Benioff desire to redistribute responsibilities and reduce his workload, appointing Taylor (or another executive) as co-CEO could be a viable solution. Brent Leary, principal analyst at CRM Essentials, also notes Taylor’s expanding role within the company, supporting this possibility.

“Following the acquisition of Quip, Taylor experienced rapid advancement, becoming president and chief product officer within a year and a half, and subsequently being promoted to chief operating officer two years later,” Leary stated.

Who else could be in line?

Although Taylor appears to be a leading candidate to succeed Benioff, he is not the sole possibility, particularly considering his instrumental role in finalizing the recent $27.7 billion acquisition of Slack.

Leary observed that Benioff’s public acknowledgment of Taylor’s substantial contribution to the Slack acquisition—Salesforce’s largest to date—demonstrates the extent to which Taylor has established himself as a key figure in the organization’s most important decisions.

However, Mueller suggests that Taylor’s swift advancement might also indicate shortcomings within the existing internal talent pool, specifically concerning product development. He stated that while Taylor is a capable and intelligent leader, his ascent highlights the challenges Salesforce faces in building a strong product organization.

Nevertheless, the Slack deal also introduces Butterfield, Slack’s CEO, who will continue to lead his company, mirroring the leadership structure with Adam Selipsky at Tableau and Brent Hayward at Mulesoft. These three leaders were pivotal in developing their respective companies before successfully selling them to Salesforce for significant amounts—$15.7 billion for Tableau (acquired last year) and $6.5 billion for Mulesoft (acquired in 2018).

These individuals are also accomplished leaders. Butterfield guided Slack’s growth from its inception to a $7 billion valuation prior to its 2019 IPO, and has a proven track record of executive success, despite the size difference between Slack and Salesforce.

Hayward has been with Tableau since 2013 and, like Benioff, possesses a strong sales background and prior experience at Oracle, similar to Block’s history. Selipsky presents an even more compelling option, having spent over ten years as an executive at AWS, including the role of Chief Operating Officer, where he was instrumental in building the cloud division into a multi-billion dollar enterprise.

However, Mueller notes that there is a possibility that founders may depart once their contractual commitments are fulfilled. He explained that acquisitions often aim to strengthen the leadership bench, but this benefit frequently diminishes as time passes and initial agreements expire.

He also expresses doubt that executives joining through acquisitions will fully embrace the company culture to the extent necessary to assume the role of CEO. “Cultural integration and adapting to scale are often difficult for acquired company executives. Even in acqui-hire situations, we rarely see executives thrive, as the ‘not invented here’ mentality and the awareness of being an acquisition can be significant obstacles,” Mueller said.

Other potential candidates include Alex Dayan, president and chief strategy officer, who has been with Salesforce since 2008, and Gavin Patterson, president and chief revenue officer, who joined in May from British Telecom, bringing extensive sales experience and executive leadership.

The executive suite also includes a number of highly-placed women and people of color, such as Amy Weaver, president and chief legal officer, Tony Prophet, chief equality officer, and Ebony Beckwith, chief philanthropy officer and CEO of the Salesforce Foundation; however, these individuals do not currently appear to be pursuing the CEO position.

What will Benioff do?

To understand potential future actions by Benioff, examining the career path of his mentor, Larry Ellison – chairman and CTO of Oracle – is insightful. Ellison was the driving force behind Benioff’s launch of Salesforce more than two decades ago. Currently 76 years old, and two decades older than Benioff, Ellison remains actively engaged in the company he founded in 1977, continuing to effectively lead it.

Throughout his tenure, Ellison has held various positions. He relinquished the CEO position in 2014, while retaining the roles of executive chairman and chief technology officer. At that time, he divided the CEO responsibilities between Mark Hurd and Safra Catz. Following Hurd’s passing last year, Catz assumed the sole CEO role.

Whether Benioff will emulate Ellison’s longevity and remain with the company for another two decades remains uncertain. However, it’s evident that Salesforce possesses a wealth of capable executive leadership, prepared to assume greater responsibility should Benioff choose to retire or reduce his involvement. The organization appears well-positioned for continued success, with numerous qualified candidates to succeed him.