Ms. Huffington’s influence at Uber is growing while the company is dealing with a vacuum of leadership. As Uber tackles the fallout from investigations into its corporate culture, including allegations of sexual harassment and questions over its management, Mr. Kalanick has taken an indefinite leave of absence and left management to a committee of executives. The board is also in flux with the resignation of David Bonderman, a partner at the private equity firm TPG, after he made a sexist comment in response to her at an Uber meeting.

It now falls to Ms. Huffington, Ms. Martello and Bill Gurley, another board member and a partner at the venture capital firm Benchmark, to complete some of the urgent tasks at Uber, like vetting candidates for a chief operating officer. Prospects include David Cush, the former chief executive of Virgin America, according to two people with knowledge of the talks, who asked not to be identified because the proceedings were confidential. Mr. Cush did not immediately return a request for comment.

Ms. Huffington’s role has caused some discomfort. Some Uber executives have grown wary of her close ties with Mr. Kalanick, according to three employees close to executive deliberations. (Ms. Huffington recently visited the hospital where Mr. Kalanick’s father, who was injured in a boating accident, was staying, according to two people with knowledge of the event.) Four former Huffington Post employees also raised an eyebrow at Ms. Huffington’s ability to swoop in and quickly win people over.

Others praised her effectiveness. “She sows the seeds of trust and makes you feel her interests are aligned with yours,” said Fred Harman, a partner at Oak Investment Partners, which invested in The Huffington Post. “When you get down to making decisions, you can focus on how persuasive she is.”

In an interview, Ms. Huffington, 66, said: “Knowing how to deal with crises without being overwhelmed — keeping one’s head while people all around are losing theirs — is the most important leadership quality. In times of crisis, people often overreact and move into very dark places where they have a hard time seeing their way out.”

How Uber’s Brash Approach Is Beginning to Backfire

The company, with its co-founder Travis Kalanick, is known for its brash, aggressive approach. That approach has taken a toll.


Uber declined to comment for this article.

Ms. Huffington’s rise at Uber is the latest chapter in a life marked by dramatic career shifts that included political pundit, media mogul and corporate fixer. Born Ariadne-Anna Stasinopoulous, she grew up in modest circumstances in Greece and England, attended Cambridge University on a scholarship and became the first foreigner to be president of the Cambridge Union debating society.

She moved to New York City in 1980 and wrote best-selling biographies of Pablo Picasso and Maria Callas. In 1986, she married the oil scion Michael Huffington, whom she helped vault into national politics. Ann Getty, the socialite who had introduced the Huffingtons, was the matron of honor. The publisher Mort Zuckerman, her former boyfriend, was an usher.

After divorcing Mr. Huffington in 1997, Ms. Huffington became known for switching allegiances from Newt Gingrich and the Republican Party to the world of left-wing satire. She became a household name in 2005 with the founding of The Huffington Post, an online publication, with the venture capitalist Kenneth Lerer and Jonah Peretti, who later went on to create BuzzFeed.

Even though Ms. Huffington did not have a traditional media background, Mr. Peretti said, her ability to bring together politicians, businesspeople and celebrities was crucial. “We wanted to bring those worlds online, and she was the perfect person to do it,” he said.

In 2011, Ms. Huffington drove The Huffington Post’s sale to AOL for $315 million. She had struck up a fast friendship with Tim Armstrong, the chief executive of AOL, at the end of 2010. By January, they were negotiating acquisition details at Davos. The deal was announced in February.

Some Huffington Post board members wanted to take the company public, but Ms. Huffington was “persuasive in convincing the board that a bird in the hand at a compelling valuation was the better path,” said Mr. Harman, who was on the board.

A year later, Ms. Huffington met Mr. Kalanick at a technology conference in Munich, and the two bonded over Uber’s potential to solve big urban problems. “I was interested in not just what Uber had achieved, but in its future,” said Ms. Huffington, who later founded Thrive Global, a health and wellness business, in 2016.

She was soon advising Mr. Kalanick. When Uber announced last year that Ms. Huffington had joined the board, it released a video that featured a softer side of Mr. Kalanick and a warm, maternal voice-over from Ms. Huffington.

“Her guidance has been invaluable to me personally over the years, and I know that in this new role she’ll help take Uber to the next level,” Mr. Kalanick said in the announcement.

Photo

Wan Ling Martello, the chief of Nestlé in Asia, in 2014. She joined Uber’s board this month at Ms. Huffington’s recommendation.

Credit
Denis Balibouse/Reuters

They have sometimes disagreed, as they did when Ms. Huffington backed the board’s desire to put Emil Michael on leave, according to two people with knowledge of that discussion. Through a spokesman, Mr. Kalanick declined to comment for this article.

More recently, Ms. Huffington has been steadfast in supporting Mr. Kalanick even as other allegiances have frayed — notably his relationship with Mr. Bonderman, who had grown more concerned about Uber’s management quality, according to one person familiar with the board’s conversations. TPG declined to comment.

At an Uber staff meeting on Tuesday, Ms. Huffington spoke about how having one woman on a board often led to more women joining.

“Actually, what it shows is that it’s much more likely to be more talking,” Mr. Bonderman responded.

Ms. Huffington declined to discuss board dynamics but said Mr. Bonderman’s resignation, just hours after the gaffe, was “a huge statement about how willing the company is to live by new cultural values.”

Ms. Huffington has been particularly effective in bringing more women into Uber’s leadership, including Ms. Martello.

In January, Ms. Huffington also approached Bozoma A. Saint John, an Apple executive, at a private dinner for marketers at the giant technology conference, CES, in Las Vegas. Conversation gave way to selfies, and Ms. Saint John invited Ms. Huffington to her birthday party. For that occasion, Ms. Huffington brought Ms. Saint John a special bed for her phone — sold by Thrive Global — to be kept in another room while she slept.

In March, Ms. Huffington broached the topic of Uber to Ms. Saint John. Mr. Kalanick, she said, was on a journey of self-improvement. As they talked about how to tell a different, more human story about what Uber had to offer, Ms. Huffington had an epiphany. “She said, ‘Why don’t you tell Travis these things yourself?’” Ms. Saint John said.

Ms. Huffington arranged for the two to meet in April at her home in Brentwood, Calif., where they spoke for nearly eight hours. After Ms. Saint John left Apple last month, she knew there was only one place she wanted to work. She joined Uber in the newly created role of chief brand officer.

“Arianna gave me all of the problems at Uber straight, no chaser,” Ms. Saint John said. “It’s the magic of what makes her so believable.”

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