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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.”

Salesforce co-CEO Marc Benioff on Bret Taylor's departure from the company

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

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

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Meta’s big antitrust win, Salesforce’s deal closure, and iPhone’s popularity in China

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Meta's big antitrust win, Salesforce's deal closure, and iPhone's popularity in China

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Meta wins FTC antitrust trial that focused on WhatsApp, Instagram

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Meta wins FTC antitrust trial that focused on WhatsApp, Instagram

Meta CEO Mark Zuckerberg appears at the Meta Connect event in Menlo Park, California, on Sept. 25, 2024.

David Paul Morris | Bloomberg | Getty Images

Meta won its high-profile antitrust case against the Federal Trade Commission, which had accused the company of holding a monopoly in social networking.

In a memorandum opinion released Tuesday, Judge James Boasberg of the U.S. District Court in Washington, D.C., said the FTC failed to prove its argument. The case, initially filed by the FTC five years ago, centered on Meta’s acquisitions of Instagram and WhatsApp.

“Whether or not Meta enjoyed monopoly power in the past, though, the agency must show that it continues to hold such power now,” Boasberg said in the filing. “The Court’s verdict today determines that the FTC has not done so. A judgment so stating shall issue this day.”

Boasberg dismissed the case in 2021, saying the agency didn’t have enough evidence to prove “Facebook holds market power.” In August of that year, the FTC filed an amended complaint with more details about the company’s user numbers and metrics relative to competitors like Snapchat, the now-defunct Google+ social network and Myspace.

After reviewing the amendments, Boasberg in 2022 ruled that the case could proceed, saying the FTC had presented more details than before.

Meta CEO Mark Zuckerberg, former operating chief Sheryl Sandberg, Instagram co-founder Kevin Systrom and other current and former Meta executives all testified in the trial, which began in April.

Meta shares were little changed on Tuesday. The stock is up about 2% for the year, badly underperforming broader indexes and most of its megacap tech peers.

“The Court’s decision today recognizes that Meta faces fierce competition,” the company said in a statement. “Our products are beneficial for people and businesses and exemplify American innovation and economic growth. We look forward to continuing to partner with the Administration and to invest in America.” 

The FTC didn’t immediately respond to a request for comment.  

The ruling comes a little over two months after Google avoided the harshest possible penalty from an antitrust case it lost last year. While Google was found to hold an illegal monopoly in its core market of internet search, U.S. District Judge Amit Mehta decided the company would not be forced to sell its Chrome browser, bucking the Department of Justice’s request. Google was, however, ordered to loosen its hold on search data.

Former FTC Chair Lina Khan on Meta antitrust trial regarding Instagram, WhatsApp ownership

In the Meta case, the FTC claimed the company shouldn’t have been allowed to buy Instagram for $1 billion in 2012 and WhatsApp for $19 billion in 2014, and the agency called for those units to be divested. The commission also alleged that there were no major alternatives for apps like Facebook and Instagram that people use to communicate with friends and family in a online, social space.

However, a major challenge for the FTC, according to the judge, was in proving that Meta is breaking antitrust law today, not years ago when the primary use of social networks was very different and based on sharing other kinds of content.

“To win the permanent injunction that it seeks here, the FTC must prove a current or imminent legal violation,” he wrote.

Boasberg ultimately sided with Meta’s argument that the technology industry has evolved since the early days of Facebook, and the company now faces a wide variety of competitors like TikTok.

“While each of Meta’s empirical showings can be quibbled with, they all tell a consistent story: people treat TikTok and YouTube as substitutes for Facebook and Instagram, and the amount of competitive overlap is economically important,” Boasberg wrote. “Against that unmistakable pattern, the FTC offers no empirical evidence of substitution whatsoever.”

Big changes in social

Much of Judge Boasberg’s conclusion was built on the transformation that’s taken place in the social media market in recent years and Meta’s changing position within it. User trends have moved heavily in the direction of video, where TikTok and YouTube have massive user bases and huge network effects.

“The most-used part of Meta’s apps is thus indistinguishable from the offerings on TikTok and YouTube,” Boasberg wrote.

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Waymo says it will launch in more Texas and Florida cities in 2026

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Waymo says it will launch in more Texas and Florida cities in 2026

A Waymo autonomous self-driving Jaguar taxi drives along a street on March 14, 2024 in Los Angeles, California.

Mario Tama | Getty Images

Waymo on Tuesday said it will bring its robotaxi service to new cities in Texas and Florida in 2026.

The Alphabet-owned company said it plans to start operating its vehicles with no human driver assistants in Dallas, Houston, San Antonio, Miami and Orlando in the coming weeks before opening service in those markets to the public next year, the company said in a blog.

“Waymo has entered a new phase of commercial scale, doubling the number of cities we operate without a human specialist in the car,” Waymo Chief Product Officer Saswat Panigrahi said in an emailed statement Tuesday.

Waymo had previously announced plans to launch its robotaxi service in Dallas and Miami in 2026, but Tuesday was the first time the company said it planned to launch service next year in the other cities. Waymo will first offer fully autonomous trips to its employees in those markets, a spokesperson said.

The company has been gearing up to expand its paid robotaxis service in 2026. The company previously announced plans to expand to Detroit, Las Vegas, Nashville, San Diego, Washington, D.C., and London in 2026.

Waymo has also begun testing vehicles in New York City and Tokyo.

Last week, Waymo began offering freeway routes in the San Francisco, Phoenix and Los Angeles markets. The Google sister company will gradually extend freeway trips to more riders and locations over time.

Already, Waymo operates its paid robotaxi service in Austin, San Francisco, Phoenix, Atlanta and Los Angeles. The company has provided more than 10 million paid rides since first launching in 2020, the company said in May.

Waymo’s Florida and Texas expansion announcement comes the same day that Amazon-owned Zoox began allowing select San Francisco users to hail its driverless vehicles. San Francisco is the second market where Zoox now offers a free service, after its launch in Las Vegas in September. Zoox has deployed a fleet of 50 robotaxis between San Francisco and Las Vegas, the company told CNBC in September.

WATCH: Waymo launches paid robotaxi rides on freeways

Watch: Waymo launches paid robotaxi rides on freeways

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