Linda Jaccarino claimed that three weeks ago, billionaire entrepreneur Elon Musk had little changed when she merged with Xa and his artificial intelligence group, the social platform she was heading to.
“I’m X’s CEO and my boss remains the same,” she told the Financial Times in an interview at the Cannes Advertising Conference.
Within three weeks, neither was true.
Yaccarino announced Wednesday that he resigned from his role as CEO two years later, saying that X has “entered a new chapter” in his partnership with Xai.
Industry insiders say Jaccarino was set to fail in many ways.
She was tasked with bringing advertising dollars back to platforms that politically biased owners told brands they didn’t spend “fucking themselves.”
Musk began to put more pressure on Jaccarino, and the pair failed to ger, said the four people who worked with both of them. The billionaire’s dull style clashed with his deputy Madison Avenue Polish.
“Sheryl (Sandberg) found a rhythm with Mark (Zuckerberg),” said one of those who mentioned the former chief operating officer of Meta and its CEO, respectively. “Linda couldn’t find a rhythm with Elon.”
She boosted X’s advertising business. But after Mask AI group Xai bought the X for $45 billion in March, “she had to wonder why she was there,” said Brian Wieser of Madison & Wall, an ad consultant.
Given XK’s 24-hour round-trip approach to the main X, Yaccarino didn’t have the controls that most CEOs enjoy.
For the past six months, Musk has been distracted by his work with the Donald Trump administration.
The billionaire entrepreneur has reverted his eyesight back to his business in recent weeks and began making one-sided decisions with X. His movements sometimes blinded her and her team.
“Elon calls out every shot,” said an ad executive who knows Jaccarino and Mask. “She tried to get on the tiger, but was thrown away.”
Jaccarino, known in the industry as the “velvet hammer,” joined X in 2023 after running NBCuniversal’s advertising business.
She was given the task of begging for advertising dollars after the brand remained in large numbers following the takeover of Musk’s $202 billion platform.
Beyond advertising, she boosted X’s video capabilities, signed contracts with creators and sports leagues, and developed X Money, digital wallets and peer-to-peer payment services.
Jaccarino remained publicly loyal to Musk until the end. But those who worked with them believed her talent as a perfect sales person would hurt her relationship with him.
Musk felt that Jaccarino was not completely transparent about the company’s position with advertisers, and he placed a gloss on reality. He hoped that she would recover her business to financial health more quickly.
“He didn’t dig her style as an executive on shiny, flashy Madison Avenue,” said one person who worked with both. “He wants to have a real conversation and not come out.”
Tensions were about a year ago when Musk warned Jaccarino to accelerate growth, temporarily calling Li during Steve Davis to review X’s finances and performance management. The billionaire later hired former Tubi executive Mahmoud Reza Banti as chief financial officer.
Banti reported directly to Musk, frequently speaking to him, cutting out the chief executive, one said. Jaccarino’s relationship with Banti quickly became tense, said someone familiar with the matter.
Yaccarino wanted to allocate the budget to the Content Creator Fund and strengthen X’s advertising technology, but people said Banki questioned her spending decisions, directed investments in other areas of the company, and enacted economic austerity.
Musk’s relationship with Jaccarino shook after securing a content deal with former CNN anchor Don Lemon in early 2024, later exploded. After agreeing to the deal, Lemon conducted a controversial interview with Musk, where he asked if he had abused the drug, infuriating the billionaire who had cancelled the partnership. Lemon is currently suing Mask and X for breach of contract.
The pressure put a strain on Jaccarino, several people who worked with her explained that she occasionally shed tears in the office.
Others are paying attention to her toughness. “She went on for two years, a job that crushed most people in two weeks,” the former colleague said.
Jaccarino also won a fierce battle to bring some advertisers back to the platform.
A year after the acquisition of Mask, ads fell by about 50%. Yaccarino has turned on some of the world’s biggest brands by suing several companies, such as Shell and Pinterest, for anti-competitive behaviour. X denounced them for “illegal boycotts” of the platform.
Mask’s flowering relationship with Trump has been added to pressure on the brand, which is beginning to return to X.
X has been citing “large and well-known brands” since January, citing “large and well-known brands” such as Temu, Amazon, Apple, Google, Verizon and Dell.
Research firm Emarketer Projects X’s revenues will rise to $2.3 billion this year, compared to $19 billion a year ago. The global revenues of 2022, when Musk took over, were $4.1 billion.
However, some advertisers responsively with the Yaccarino method.
“To her credit, she has brought the advertiser back to X,” said a longtime ad executive. “She did that with a gun, but they came back.”
Advertisers did not return “voluntarily or happy,” Wieser said. For some people, it’s better to “use something” to avoid X’s legal challenges.
Some marketing executives said toxic content is not the only problem. Yaccarino has failed to make X an effective advertising platform that provides return on investment, they said.
“She can argue that she hasn’t done enough to improve the platform for advertising,” said one advertising executive. “Many clients don’t advertise on X because they don’t work very well, not because of content.”
Still, Jaccarino appears to be on the roll despite being financially constrained, with some insiders celebrating her legacy. “It was Linda’s motivation, energy and mercy that helped me restructure some of these relationships,” the former colleague said.
Things changed when Musk returned from his extended foray into politics.
“It was the election that saved her, and Elon jumped deep into the administration, and then he took his eyes off a bit,” said one person who worked with them.
The merger with Xai came when Musk returned his focus to the company.
“Now he’s back in his business, so he never made her the head of an AI company,” the person said.
In recent weeks, Musk has made several unilateral decisions about advertising, people familiar with the issue said. He bans hashtags from the ads and announces that X will charge the brand based on vertical size. He also hired Nikita Bier, an entrepreneur and high-profile X user, as head of product.
Jaccarino thought the masks were not focused sufficiently safely. According to anyone familiar with the issue, it is an important issue for her.
Jaccarino informed some choices before her departure. According to X staff, this spewed anti-Semitic hatred with Xai’s Grok Chatbot on Wednesday, but spewed anti-Semitic hatred.
X and Yaccarino declined to comment. Musk did not reply to requests for comment.
It is unclear what will come next for ad veterans. His unwavering support for Trump and Musk, known as devoted Republicans, has surprised many of his ad companions.
According to industry insiders, her long-standing defense of masks could hinder the CEO’s role in another media or entertainment company.
However, X’s role helped to boost her connection in Washington.
She personally knows Trump’s daughter Ivanka Trump, who brokered her relationship with the president, said those familiar with the matter.
She is also close friends with Scott Turner, the current secretary of the Housing and Urban Development Agency, and director of Intelligence Tarsi Gabbard. A longtime best friend said Jaccarino continued to support Trump despite the explosion with Musk.
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Some suspect that her next move is to serve as a defence in administration or as a free speech advocate. Yaccarino began wearing diamond-studded necklaces after reading “Freedom of Speech” in X’s leadership for about a year.
Mike Benz, a Trump first administration official, now runs the Free Speech Watchdog, but after resigned, he praised Jaccarino with X.
“She stepped up for all of us in the face of what appeared to be insurmountable pressure from governments, advertisers, boycotters, banking institutions and starry lynching mobs,” he wrote. Jaccarino later shared the post.
“Before X, she was on Mount Rushmore, an advertising executive,” said Lu Pascalis, CEO of Marketing Consultant AJL Advisory. “She doesn’t need to work, but she needs to go out in style, and I think that’s the next thing for her.”
Additional Reports by Daniel Thomas
