Linda Yaccarino was in full flow when a text message from a friend stopped her in her tracks. It was May 11 and the head of global advertising for NBCUniversal was rehearsing for upfronts, the annual showcase of forthcoming television programming designed to woo marketers. The event, due to take place four days later at Radio City Music Hall, would put Yaccarino in her comfort zone: centre stage.

Prepping in a conference room on the 51st floor of 30 Rockefeller Plaza, the New York headquarters of NBC Studios, Yaccarino had been making edits to her teleprompter text with a small group including her deputy, Joe Benarroch. As they worked, Yaccarino had unknowingly become the subject of a global breaking news story after Elon Musk tweeted: “Excited to announce that I’ve hired a new CEO for X/Twitter. She will be starting in ~6 weeks!”

The incoming message on Yaccarino’s phone read: “Is ‘she’ you …?”

She was.

Musk’s post followed weeks of criticism of his caustic management of one of the world’s top social media sites. More than six months had passed since he’d bought Twitter, later renamed X, for $44 billion (€41.2 billion). But the bankers and investors who had helped the mercurial billionaire close the deal were still waiting for clarity on the company’s long-term leadership. In December, Musk polled his millions of followers asking whether he should step down as acting CEO. The majority of respondents said he should.

By May 11, Yaccarino and Musk had been tentatively discussing the chief executive job for several days. According to people familiar with the matter, she’d told Musk that morning that she would accept the position but needed several weeks to wrap up her NBCUniversal tenure. Yaccarino was managing a team of thousands and oversaw more than $10 billion in annual revenue, so her departure had to be handled appropriately. Yet with one characteristically sensational tweet, Musk had blindsided her and now she, in turn, looked as though she had blindsided NBCUniversal.

Yaccarino pulled Benarroch aside and showed him Musk’s post. “We need to leave the building,” he whispered. “Right now.”

She turned casually to her colleagues: “I just need to pop to my office!” Instead, she dashed home to try to figure out how to smooth over the situation.

When Yaccarino spoke to Michael Cavanagh, president of Comcast, NBCUniversal’s parent company, in an effort to explain what had happened, he voiced his fullest support of her new opportunity, according to several people familiar with the matter. She offered to hold off confirming the move and present as planned. But Cavanagh didn’t think that NBCUniversal could withhold such significant information. He wanted to issue a press release about her exit the following morning.

That’s how in early June, Yaccarino began a new chapter in arguably the toughest job in tech. She is tasked with resuscitating a company that has appeared to teeter on the edge of collapse, as its workforce was gutted, advertising dwindled and multiple competitors launched copycat alternatives. To do that, she must bring advertisers back to the capricious new owner who, in 2019, tweeted: “I hate advertising.”

During the CEO search, Musk acknowledged on Twitter that he was seeking someone “foolish enough to take the job”. He remains the chief technology officer, executive chair and owner of X. His grip on the company complicates Yaccarino’s leadership and risks undermining or embarrassing her. Big announcements, such as the X rebrand or the August proposal to scrap the site’s blocking feature have come from Musk, not Yaccarino. Marketers find some of his tweets galling. In the latest bout of turbulence, Musk threatened to sue the Anti-Defamation League (ADL), the civil-rights group that fights anti-Semitism, just days after Yaccarino boasted that the platform was building a productive partnership with the organisation.

Yaccarino’s critics say that Musk’s impulsive front-running on the CEO announcement was merely a prelude and that she has appeared on the back foot on multiple occasions since. Taking on the role has required sacrificing some integrity, they claim, becoming a puppet in Musk’s regime. “The job is not to be CEO,” says one person with knowledge of their working relationship. “You will not get to control Elon, you have to roll with the punches and channel him. If he says the sky is bright pink, you have to say you’re excited the sky is pink.” Lou Paskalis, a former top media executive at Bank of America and a long-standing Yaccarino confidante, doubts Musk’s ability to hand over the reins at all. “Since the hire, it seems to me, whether consciously or subconsciously, most of his actions seem to sabotage her success,” he says.

Since Yaccarino came on-board, the frenzied circus around Musk has only intensified. A major biography written by journalist Walter Isaacson and a number of in-depth investigations have generated ceaseless headlines about everything from the geopolitical clout conferred upon Musk by his Starlink internet satellites to the Kardashian-level complexity of his romantic entanglements. Fewer column inches have been dedicated to Yaccarino. This is the first time she has spoken at length to the press. She sat down for four exclusive interviews over the course of several weeks to reflect on her first 100 days in the job. It has been a baptism of fire by many accounts, including hers.

“Elon talks about it a lot – that the feedback loop on X is one of the most powerful things. But you have to get comfortable with that negative feedback loop, and it’s sobering. It’s humbling.” Locking eyes with me through her trademark chunky designer glasses, Yaccarino is making the hard sell for chaos. She is 60, small in stature, but with the command of a seasoned media executive, her voice occasionally dipping into a New York accent. Yaccarino says she was drawn to X because of this relentless pace, which offers “intoxicating liberation, freedom to move quickly and to innovate and iterate in real time”.

There is a dogma in Silicon Valley, once exemplified by Steve Jobs, that minimalism in all facets of life, including personal style, yields extra productivity. Parag Agrawal, Twitter’s chief executive before the Musk take­over, wore the same outfit to the office every day: a black T-shirt and dark blue jeans. By contrast, Yaccarino, the Long Island-born-and-raised Madison Avenue power broker, is all show business. She’s wearing a silk shirt, white leather trousers and glittering stiletto heels, her wrists and fingers dripping in jewellery. A diamond-studded necklace reading “Mama” hangs around her neck.

We’re at X’s New York office, in an unmarked Manhattan high-rise, sitting in the canteen once known as “the commons”, now dubbed “NYX”. The walls and pillars are plastered with screens beaming out the new X logo. Despite Musk’s recent decision to do away with the Twitter name and emblem, remnants of the old branding remain. Corporate security staff still have the little blue bird sewn on to their black polo shirts; the guest wifi password is avian adjacent. Like the platform, this is a site in flux.

On arrival, I’m handed a guest pass that mistakenly designates me a photographer not a reporter. The security guard apologises, adding cheerfully: “Well, we don’t want people throwing things at you anyway!” Musk has made no secret of his distaste for what he calls the mainstream media. Until recently, journalist inquiries to X’s press department received an auto-response of a poop emoji.

Yaccarino, attempting to usher in a friendlier era, greets me warmly. During the time we spend together over several weeks, it’s clear she wants me to understand that she made it to the helm of X through intention, calculation and hard work. She attributes this, in part, to a highly supportive upbringing. Yaccarino still lives in Long Island, a half-hour’s drive from where she grew up in a first-generation Italian-American family, the daughter of a retired Nassau County police chief and a homemaker. Her identical twin is a nurse practitioner and their sister is a former Deutsche Bank managing director. Yaccarino has two children with her husband, a designer and commercial contractor who she met soon after college on a blind date, and one grandchild.

Yaccarino started working in marketing soon after graduating from Penn State University, where she studied liberal arts and telecommunications. She had won an editorial internship at a local NBC affiliate but, due to a bureaucratic error, was assigned to the sales department. Where Musk’s biographer recently described him to the FT as without “empathy”, advertising industry insiders portray Yaccarino as a consummate networker and relationship builder. She’s fun, they say. A friend, a force. “Good to the bone,” says Shelley Zalis, founder of gender equality group The Female Quotient, who has been close to Yaccarino for years. Also: “a badass … grace with grit.”

Yaccarino knows her draw. “Historically, throughout my career at very big, multinational companies, I’ve tended to gather people along the way.” She tends to bring those people with her. Benarroch immediately joined her at X, leading business operations. Recently, X hired Carrie Stimmel as global agency leader and Monique Pintarelli as head of the Americas. Yaccarino worked with them at NBCUniversal and Turner Broadcasting respectively.

Her career took off during a period of rapid change for media, beginning in the early-2000s. Digital companies such as Google, Facebook (now Meta) and Netflix disrupted traditional models and legacy competition morphed continuously as a result of major acquisitions and consolidation. “The ground beneath our feet kept changing,” she says. The biggest test of her mettle came when she was called on to reshape the ads business in the wake of Comcast’s $17 billion acquisition of NBCUniversal in 2013. She embarked on a strategy of stitching together the individual network brands. “My more tactical mantra was, we need to become easier to do business with,” she says. Asking multiple territorial sales teams to share ideas and resources ruffled feathers. But other media outfits soon adopted the same model. “Not only did we transform our company, but it initiated a transformation of the industry.”

As the pace of change ramped up in recent years, Yaccarino raced to keep up. She played a role in developing NBCUniversal’s programmatic advertising, or automated media buying. She helped pitch and launch Peacock, Comcast’s streaming service, in 2020, generating $1bn in upfront revenue within two years. “She took NBCU out of the dark ages and put them in the 21st century,” Paskalis says.

Amid the upheaval, Yaccarino says she developed a fixation with Twitter “for what started out as pure simple business reasons that we could make more money together and be successful together”. NBC might have captured the big screens in people’s homes, but mobile phones, she says waving her own, “paved a way to real-time conversation that NBCUniversal couldn’t do”. That “feedback loop” could help bolster shows such as Saturday Night Live, for example, or NBC’s Olympics coverage. According to multiple people familiar with the matter, Yaccarino prepared proposals for a potential Twitter acquisition on three different occasions in 2015 and 2016, urging Comcast executives to buy the platform outright. The offers were about $3 billion at the time, according to one person. While there were early conversations between the two parties, a deal never materialised.

It was not just the power of Twitter that captured Yaccarino’s imagination. She says she has long admired Musk for his leadership style and values. Earlier in her career at Turner Broadcasting, she had studied from the playbook of “visionary” Ted Turner, the media innovator so prone to speaking his mind that he was known as Captain Outrageous and who was, in many ways, the Musk of his day. Her X profile has long noted her respect for “provocative leadership” in a “wink to Turner,” she tells me. (Yaccarino never directly reported to him.)

There are those close to Yaccarino who believe she had her eye on X’s CEO job from the moment Musk took over. In her telling, she sought Musk out after the deal closed, pressing him to meet and discuss how she could make NBCUniversal a bigger media partner “via email, text, I may have been considering a homing pigeon”. She agreed to interview him at a marketing conference in Miami in April, the two of them building a rapport on stage before hosting a dinner with ad industry executives afterwards. It was “a wonderful evening, wonderful evening”, she recalls. Several weeks later, the pair discussed the CEO role at another advertising conference. “My transition to then Twitter, now X, began, and it hasn’t stopped since,” she says.

Musk, according to multiple former and current staffers, runs X from his iPhone. To break through, do not send him attachments or documents or spreadsheets. Put everything inside the body of the email. Find a way to make a simple graph fit inside the text box. Take screenshots and embed them. This is what survivors at X have learned.

For many of the self-selecting group who signed up to the mandatory pledge to adhere to his “hard-core” working culture, going the distance at X has essentially meant adjusting to the working practices of one man. For Yaccarino, the calculation will be a similar one. “The smart thing for her to do is let Elon be Elon and work with it,” says a person with knowledge of their working relationship. “That’s the trade off of getting the CEO role she’s always wanted.”

Early on, Musk brought in a team of executives and staffers from elsewhere in his business empire, including Tesla and The Boring Company, to help steady the ship. Formally, they were dubbed the “transition team”. Informally, they were known as the “goons”, according to ex-staffers. Holdovers found Musk has no tolerance for people who make nonsensical statements in order to sound smart. If you do not know something, admit it, they were told by long-time Musk employees. (Then, tell him you will get back to him on the matter in a reasonable number of hours.) They discovered he cares about working with people who are directly responsible for tasks. (Middle managers were among the first laid off when Musk took the reins.)

Unwavering loyalty is a given. Musk is intensely paranoid about the risk of “saboteurs”, disenchanted employees who might deliberately harm the company. Suril Kantaria, a Silicon Valley entrepreneur who headed finance as part of the transition team, reporting directly to Musk, says the billionaire has a “unique ability” to “create extreme urgency” that gets his team focused. “Wartime at any company is hard, but under Elon it’s next-level intense.”

The dynamic is a far cry from the era of former chief executive and co-founder Jack Dorsey, who was known for his intensely quiet, guru-like aura and yogi beard. An advocate of bitcoin and extreme health fads, Dorsey was determined to relinquish any responsibility for decision-making at Twitter, allowing staffers to debate each other into stalemate. Many blamed this approach for the sluggish pace of change at the company during the years preceding Musk.

One former senior staffer, who worked under Musk, says he seeks out employees who can balance “measured pushback” with capitulation to his whims. Another says the billionaire chooses “effective operators who are happy doing the bidding of someone else without question” over those with strong opinions. “That’s not a knock at him. He clearly has a track record of getting it right a lot.”

As a result, Musk has built a core crew of trusted lieutenants over the course of his career. These include Steve Davis, The Boring Company CEO, and Omead Afshar, who once led Tesla’s Gigafactory in Austin and is nicknamed “the Elon whisperer”. Both were brought in to X to smooth the transition. According to those familiar with the matter, Musk sees his relationship with Yaccarino as mirroring that of another long-time ally: Gwynne Shotwell, the level-headed chief operating officer and president of SpaceX, and one of the few women to work for Musk at the executive level.

Yaccarino declines to share many details of Musk’s working style. She seems caught unawares by the line of questioning. “Maybe I should take a note of what you’ve just said!” she says, laughing, when I ask about his mobile phone-first approach to communicating with staff. But she has to be available 24/7, she says, and is “in awe” of Musk’s availability and accessibility to her. The pair have very distinct business responsibilities. Musk heads up the engineering and product teams. Those developers don’t see or answer to Yaccarino in any way, insiders say. Her remit, instead, is “all business operations”, including HR, partnerships, legal, sales and finance. She describes herself as a “vagabond of sorts”, based between New York and “aeroplanes”, flying to meet advertising clients. Musk is based in Texas.

Failing to adapt to Musk’s idiosyncrasies is an unappealing prospect. In the past he has had no qualms about publicly tearing down employees and former employees. Former head of trust and safety Yoel Roth was forced to flee his home and go into hiding after resigning from the company several weeks after the takeover, when Musk turned on him, making false allegations about Roth on X. In a New York Times op-ed last week, Roth wrote: “Mr. Musk’s actions have normalised and popularised vigilante accountability and made ordinary employees of his company into even greater targets.”

Some insiders say Yaccarino has no illusions about her relationship with Musk. Perhaps, the person with knowledge of their relationship suggests, whether or not she wields real power is besides the point: it is not what Yaccarino is seen to do publicly but this perceived interpersonal dynamic with Musk that will be vital to her success. “The key question is: do people think you have influence with Elon? Do they think that you have any power?” this person says. “Can she talk him off a precipice?”

For her part, Yaccarino says a positive working relationship with Musk requires “being successful at your job. Question every history, every legacy. He talks a lot about principles, so you’re constantly asking yourself: why are we doing that? How could we do it better?” Every so often, she veers into corporate speak or backtracks. (On one occasion, she asks: “Did I answer your question? I want to make sure because I don’t think I’m perfect.”) There have also been major gaffes. She was forced to delete a new video showing her vision for X, intended to lure back advertisers, after users noticed it featured unsavoury tweets in the background.

Still, Yaccarino has successfully pushed some of her own priorities at X. In September, she revived the company’s “client council”, an invitation-only group of marketing and advertising agency executives. She also struck a deal with Google for the search giant to sell X’s advertising space, though the outsourcing was seen by some as a sign of desperation to generate revenue. Recently, Yaccarino requested more engineering resources to improve X’s advertising technology, according to three people familiar with the matter. It was a bold ask in the era of a leaner X, but she eventually received approval to make the hires, one of the people says. I ask Yaccarino if she thinks she can forge a long-term executive relationship with Musk. “I heard recently that, of his executive team, they stay together for more than a decade,” she answers. “So I am hoping that I have at least nine years and 42 weeks left.”

It was November 3 2022, just days after Musk had somewhat reluctantly closed the deal to buy Twitter. The new owner was on a call with marketers and advertising executives. The conversation was intended to placate numerous concerns. First, there were immediate fears that the platform was being overrun by toxic content as Musk, a self-declared “free-speech absolutist”, stripped back moderation policies and laid off employees. There was also the question of his own tweets.

Musk has not been shy about sharing sometimes fringe viewpoints and baseless conspiracy theories, railing against “woke culture”. Recently, he tweeted that he supported British comedian Russell Brand, who is facing rape and sexual assault allegations.

After Musk presented his vision for the platform, attendees were mostly deferential during a Q&A session. But then Linda Boff, the chief marketing officer of General Electric, spoke up to ask Musk about his tolerance for hate on the platform, given brands’ fears of showing up next to harmful content and misinformation. Attendees shifted uncomfortably in their seats. One person who was on the call says he gave a non-answer. “He was matter of fact,” says another, “that Elon is going to be Elon.” Boff declined to comment.

Musk, according to insiders, is focused on innovating X’s user experience for one end-user in particular: himself. And he intends to use it exactly as he pleases. As his behaviour became inextricable from his platform, brands pulled their advertising or drastically cut how much they spent. Musk has called some chief executives personally to berate them and threatened to “name and shame” others. As a private company, X is no longer required to disclose detailed financials. X says that 90 per cent of 2022′s top 100 spenders globally have now resumed spending. But ad revenue in the US is still down 60 per cent, Musk said this month. And data from analysts SensorTower suggests that 43 out of the top 100 advertisers before the acquisition are still not spending on the platform in the US as of August. For many of those who have returned, the level of spending is far lower than before, according to SensorTower.

That means Yaccarino has a gargantuan set of tasks in advance of her. But curbing Musk’s use of X is not on her agenda. “What binds us together is our belief in the freedom of speech and the freedom of expression,” she tells me, not for the first or last time. Freedom of speech “only works when someone you don’t agree with says something you don’t agree with”. Yaccarino says this carefully, weighing each word and attributes the sentiment to Musk.

While Musk has claimed to have voted for Democrats in the past, he now has a tendency to court Republicans, such as the rightwing commentator Tucker Carlson. Colleagues and confidants describe Yaccarino as a conservative. But when I ask about her personal politics, she baulks. “I don’t think that’s material to this discussion.” I counter that some would argue free speech is being politicised, that letting misinformation, racism or sexism run rampant on the site is not really in the interest of the public forum. “I cannot process the question,” she says. “How is freedom of speech politicised? It is one of the foundational core values of what this country was formed on, so I don’t really understand how that’s a political issue. I think that would be something everyone, no matter what your opinions are, would agree on.”

The silence that follows begins to feel awkward. It’s one of several moments where Yaccarino stonewalls. She’d rather pivot to the new tools she has set up to ensure adverts run alongside “healthy” content, a move welcomed by advertisers I have spoken with. She repeats the catchphrase “freedom of speech, not reach” and asserts that X is successfully restricting the impressions of “lawful but awful” posts. She teases the imminent launch of vertical video advertising, as well as the announcement of new “content relationships” – forthcoming tie-ups with celebrities such as Paris Hilton. During her initial weeks in the role, Yaccarino met major Hollywood talent agencies, as well as Brian Rolapp, the CEO of the NFL, and NBA executive Bill Koenig, according to multiple people familiar with the matter. After a “turbulent time”, X is “pivoting towards growth”, she insists. “The platform is showing good signs of momentum.”

Yaccarino’s tendency towards positivity has not gone unnoticed by users of X. She has been widely mocked for her bright and breezy posts, which make for a stark contrast with Musk’s. I ask, twice, about concerns that policymaking is ad hoc and opaque. Yaccarino swerves, answering that the company has “dedicated” teams for trust and safety, brand safety and protecting children. I ask what happened to the “content moderation council with widely diverse viewpoints” that Musk said he would set up when he first took the helm to dictate policy and review major account reinstatements. “That is news to me,” she says. “You’re the first person that mentioned that.”

Then there’s the ongoing spat with the ADL. In a series of posts earlier this month, Musk started engaging with a campaign that the ADL says was started by white supremacist Nick Fuentes and conspiracy theorist Alex Jones to ban the group. Musk threatened the group with a lawsuit, arguing that it had been trying to “kill this platform by falsely accusing it & me of being anti-Semitic”. Advertising revenue was down in the US, Musk claimed, “primarily due to pressure on advertisers by @ADL (that’s what advertisers tell us)“. If they pursue the case, the ADL “would potentially be on the hook for destroying half the value of the company, so roughly $22 billion”, he wrote. A matter of days before Musk’s outburst, masked men had marched in Florida chanting “Ban the ADL” and waving swastika flags, the ADL said.

The dispute came just days after Yaccarino met ADL head Jonathan Greenblatt, in what both had described publicly as a productive meeting. “The issue that’s being debated is not about supporting ADL’s mission to fight anti-Semitism. We’re all in on fighting anti-Semitism,” Yaccarino tells me. “The issue is about the ADL misrepresenting or not addressing the progress that we’ve made in our ongoing efforts.”

I ask Yaccarino, who was vocal at NBCUniversal about the need for more robust metrics and measurement in advertising, if she really believes the ADL has lost the company half of its value. She doesn’t answer. In spite of all the glowing reviews of Yaccarino from advertisers and acquaintances I heard during the course of reporting this piece, many were upset at the handling of this particular issue. One person notes that Musk already appears to be wading well out of his purported remit and into hers. To woo brands, X has to “build the trust back”, says Michael Kassan, chief executive of media consultancy MediaLink. “There has to be more transparency. It can’t be the whim of, ‘I woke up, and I want to change the name’ or ‘I woke up, and I want to change the algorithm’ or ‘I woke up, and I want to sue the ADL’. That’s the way it appears. And that’s not ever going to win the confidence of advertisers.”

Yaccarino is one of a small number of women to have run a big US tech company. Historically, Silicon Valley has not been particularly kind to female CEOs. “That responsibility of leadership is not lost on me,” Yaccarino says, during our final conversation.

Since her appointment, she has been linked with the “glass cliff” theory, put forward in 2005 by researchers at the University of Exeter. The theory posits that women are more likely to be promoted or brought into top jobs at times of a crisis and thus set up for failure. This then reinforces the gender stereotype that women are not competent leaders. “She’s supposed to clean up like mommy and, regardless of her politics, it’s almost impossible to win,” one female senior media executive tells me. “It’s bad for women in leadership.”

We haven’t discussed it when, unprompted, Yaccarino brings up her dismay at a May article in Wired headlined “Twitter CEO Linda Yaccarino Is Teetering on the Glass Cliff”. “What I was really disappointed and really kind of sad about is that there should have been consideration about previous roles and accomplishments and the tremendous potential that could happen with me taking this chair. Instead of just looking at, you know, an easy, lazy statistic,” she says. “I literally went to the business world not even knowing being a woman was a thing.”

A big test of Yaccarino’s leadership will be the 2024 US presidential election. Former president Donald Trump, who was suspended from Twitter and other platforms in the wake of the January 6 attack on the Capitol, is now back on X, though has yet to take up his previously frantic levels of posting. Yaccarino assures me X is staffing up in advance of the campaign by “expanding the safety and election teams all around the world to focus on combating things like manipulation, surfacing of inauthentic accounts and closely monitoring the platform for any emerging threats”.

If advertising dollars are not forthcoming, Yaccarino may be forced to rely on Musk’s broader plans to build X into a so-called everything app, with functionality beyond posting, such as commerce and financial services. These are notoriously difficult areas to break into, but Yaccarino insists that “voice calls, video calls and payments are right around the corner”. The company has already started charging more for access to its proprietary data. “Can Linda restore the value of the ad business of Twitter? No,” says Rob Norman, former chief digital officer at media investor GroupM. She could, however, attempt “to change the economic model of the business. If she can do that,” he adds, “then she’ll be a hero. It’ll be a triumph.”

Those close to Yaccarino say there is still a chance moving to X could look like a stroke of genius, in retrospect. If she fails to deliver, the blame is likely to fall squarely on Musk. If she succeeds, she will have done the impossible. Some speculate that her ambitions exceed being chief executive of X; they say she has hinted at designs on roles such as Disney CEO. Either way, her chances will be hugely influenced by how Musk decides to exercise his freedom of speech.

Our final interview closes on a surprising note. During our conversations, Yaccarino has fiercely and consistently defended Musk’s vision for X. Even so, she seems genuinely shaken by vitriolic personal attacks. “The thing that weighs on me a great deal is the pressure and the burden of the intense and relentless public scrutiny,” she says. “I don’t know if any human being could anticipate or prepare for that. It’s hard. It’s hard on me. It’s hard on my family, my children, my parents, and that, I would say, in the first 100 days is a continual learning process to balance that.” This is what Twitter has become in its often dizzying, sometimes grotesque transformation into X. A more freewheeling forum with fewer guardrails on speech seems to have been the whole point. Yaccarino takes off her glasses for the first time. “While I did have a very outward facing or high-profile role in my last job, certainly the intensity is very different. That hits big.” – Copyright The Financial Times Limited 2023