Elon Musk’s hire of Linda Yaccarino as Twitter’s new CEO came after a whirlwind courtship — but the ad guru has had her sights on the struggling social network for nearly a decade, sources told On The Money.
Musk snagged Yaccarino earlier this month in talks that didn’t become serious until almost 24 hours before Musk’s viral tweet on May 11 that he had “a new CEO for X/Twitter,” according to sources briefed on the surprise move.
But 60-year-old Yaccarino’s relationship with Twitter was a slow burn: According to insiders, the hard-charging exec had pushed her former employer NBCUniversal to consider acquiring the social media platform multiple times.
Beginning in 2014, Yaccarino hosted three formal presentations with NBCU’s executive leadership team that outlined what a Twitter deal would look like, a source with direct knowledge said.
While executives kicked the tires, they never retained bankers or took the next step toward completing an acquisition.
Yaccarino didn’t meet Musk until about six months ago, but sources said she wasted no time showing him her vision for what the company could be.
In February, she called him up, invited him to the Possible Conference in Miami, asked to interview him onstage and even hosted an intimate dinner for him with other marketing executives at the posh Faena hotel in April.
For Musk, it was one of the first successful meetings he had with advertising execs.
Earlier this month, Musk and Yaccarino saw each other again at advertising behemoth WPP’s Stream Conference in Napa Valley where they had an hourlong conversation that ultimately cemented Musk’s decision to bring her on board.
“She has wanted it but it didn’t really happen until a day or two before” the May 11 tweet, a source with knowledge told On The Money.
People close to Yaccarino say she feels the policy Twitter unveiled last month, “freedom of speech, not reach” will make it easier for her to get more advertisers.
The new policy asserts ads will not be placed alongside any content that is flagged as problematic.
“Linda knows the marketplace, she knows the Twitter product intimately, and she knows a thing or two about big scale partnerships and has a vision,” a source who spoke on the condition of anonymity told On The Money.
“I’m pretty sure Elon saw all of that and it helped confirm his decision.”
Still, the timing was awkward.
Yaccarino’s resignation came days before the ad industry’s annual “upfronts” — when TV networks try to line up advertisers for the months ahead.
Yaccarino had been preparing for weeks ahead of the presentation – which she ended up skipping after news of her role at Twitter broke.
“A lot of people can’t get their heads around the fact that it moved that quickly,” a source close to Yaccarino said.
Now, the one organization she should be closest to – NBC – may be one of her most difficult advertising relationships to repair.
“Yaccarino wanted to exit on good terms… and then Elon Tweeted about her coming on board and the news broke and NBC went bats–t crazy,” a source close to the situation told On The Money.
“She wanted to maintain a good relationship with NBC because they do so many deals with Twitter.”
Still others told The Post that NBCU’s new chief Mike Cavanaugh is extremely supportive of her new role.
A spokesperson at NBCU declined to comment.
Sources with knowledge say Yaccarino had signaled she wanted to be a tech executive for years.
According to insiders, her name had been floated for roles at tech companies including Snap, Meta and Netflix.
“Yaccarino has been shopping herself around Silicon Valley for quite some time – she was making it known she wanted a big job in tech,” a source close to Yaccarino told On The Money.
“She was clear she definitely wanted her next chapter to be as a CEO,” another source added.
People who knew Yaccarino told On The Money this is an excellent role for her skillset.
“Linda is going to be fabulous at getting major advertisers excited about the platform,” a source told On The Money.
Another person close to Yaccarino noted she will also lean into other possible money makers including subscriptions and commerce.
Meanwhile, Yaccarino has been fending off backlash for accepting the job — with some reporters suggesting she is a classic example of a woman set up to fail at a company in crisis.
In response to an article claiming she was teetering on a “glass cliff,” she posted, “As someone used to wearing 4 inch heels, let’s be crystal clear: I don’t teeter.”