Marc Benioff, co-founder and chief executive officer of Salesforce.com Inc., speaks during the WSJDLive Global Technology Conference in Laguna Beach, California, U.S., on Wednesday, Oct. 26, 2016. The conference brings together an unmatched group of top CEOs, founders, pioneers, investors and luminaries to explore tech opportunities emerging around the world.

Patrick T. Fallon | Bloomberg | Getty Images

Turbulence in the upper ranks at Salesforce isn’t sitting well with Wall Street.

On Monday, the company announced the departure of Slack CEO Stewart Butterfield, who joined Salesforce last year as part of its biggest acquisition ever. Last Wednesday, Salesforce co-CEO Bret Taylor, who orchestrated the Slack deal, said he was leaving —exactly a year after getting promoted to share the top job with Marc Benioff.

In the three trading days since the Taylor news landed alongside Salesforce’s third-quarter earnings report, the stock has had two of its three worst days of the year, plunging 8.3% and 7.4%, respectively. Salesforce has now lost 47% of its value for the year, compared to the Nasdaq’s 28% drop, and is trading at its lowest since March 2020, the early days of the Covid-19 pandemic.

Taylor, who joined Salesforce in 2016 through the acquisition of his startup Quip, said he’d “decided to return to my entrepreneurial roots.” Benioff said on the earnings call, “We have to let him be free, let him go, and I understand, but I don’t like it.”

Butterfield made it clear that he’s leaving for different reasons.

“I’m not going to do anything entrepreneurial,” Butterfield wrote in a Slack message that was viewed by CNBC. “As hackneyed as it might sound, I really am going to spend more time with my family (as well as work on some personal projects, focus on health and generally put time into those things which [are] harder to do when one is leading a large organization).”

While Taylor and Butterfield are the highest-profile exits, they’re far from alone among Salesforce’s executive ranks.

Last month, Salesforce said Gavin Patterson, the president and strategy chief, would be leaving in January, and on Thursday Mark Nelson, president and CEO of Salesforce’s Tableau product, tweeted that it was his last day.

Along with Butterfield, Slack is losing product chief Tamar Yehoshua and Jonathan Prince, senior vice president in charge of marketing, brand and communications, people familiar with the matter previously told CNBC. Noah Weiss, senior vice president of product at Slack, will succeed Yehoshua, Butterfield said in a Slack message. Butterfield is being succeeded by Lidiane Jones, an executive vice president at Salesforce who joined in 2019.

Salesforce’s three-day plunge

CNBC

‘Two elephants in the room’

Slack was a pandemic-inspired acquisition. With workers forced to communicate remotely, Slack’s popular chat app blew up. In a series of tweets on March 25, 2020, Butterfield said the company had experienced “early signs of a surge in teams created and new paid customers unlike anything we had ever seen,” adding that the shift from email to chat channels, “which we believed to be inevitable over 5-7 years just got fast-forwarded by 18 months.”

Salesforce was so jazzed about Slack’s expansion that it paid over $27 billion for the company at a forward price-to-sales ratio of 24, one of the highest multiples ever in software. Taylor’s name was all over the deal, even though he wasn’t yet co-CEO. Taylor reached out to Butterfield multiple times in August and September 2020 about a possible acquisition, and the two negotiated throughout the process, which culminated in an agreement announced on Dec. 1 of that year, according to a filing with the SEC.

Salesforce’s purchase of Slack closed in July 2021, and its stock peaked four months later at almost $310. Since then, it’s lost 57% of its value, closing on Monday at $133.93.

Like its high-valued tech peers, Salesforce has been hurt this year by soaring inflation and rising interest rates, which have pushed investors into parts of the market deemed safer in a slowdown. Salesforce’s results haven’t helped. Last week, the company reported third-quarter revenue growth of 14%, the slowest expansion for any period since the company’s IPO in 2004. Its forecast for the fourth quarter is for growth of 8% to 10%.

In a break from third-quarter tradition, Salesforce neglected to provide guidance for its next fiscal year.

Analysts at Guggenheim wrote in a report that there were “two elephants in the room.” The first was omitting guidance for the coming year.

“The second elephant in the room is why Bret Taylor decided to give up his high-profile co-CEO and vice chair position after only a year,” wrote the Guggenheim analysts, who have the equivalent of a hold rating on the stock. The analysts reminded clients that three years ago, Keith Block resigned as co-CEO after 18 months on the job and wrote that “the company seems to have struggled since.”

After Taylor’s announcement last week, Wedbush analysts wrote that, “the Street will view this as a shocker with Taylor one of the mainstays in the CRM strategy.”

A Salesforce spokesperson declined to comment beyond reiterating a statement the company sent earlier regarding Butterfield’s departure.

On Thursday, Wolfe Research downgraded Salesforce stock to the equivalent of hold from a buy. They wrote that the company is moving into “a new and difficult chapter” after execution errors, big-name departures and slowing revenue growth.

The only day in 2022 that Salesforce’s stock has been hit harder than it was Thursday or Monday was at the very beginning of the year. On Jan. 5, UBS downgraded Salesforce and Adobe, telling clients that enterprise tech spending was pulled forward by the pandemic, leading to slower continued growth for the two companies.

WATCH: Salesforce shares under pressure after co-CEO Bret Taylor steps down