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Uber's Search for Key Comms Hire Shows Just How Serious It Is About Fighting "Asshole" Taxi

The key pick will say a lot about Uber's future intentions.

Asa Mathat

In an interview with me at the Code Conference in May, Uber CEO Travis Kalanick was pretty clear that one of his key goals for the year was to hire a big-gun communications and public relations strategy person for the transportation logistics juggernaut.

The reason? “It’s not Pinterest where people are putting up pins. You’re changing the way cities work, and that’s fundamentally a third rail,” he said in his typically forthright manner. “We’re in a political campaign, and the candidate is Uber and the opponent is an asshole named Taxi.”

Thus, the company has been aggressively seeking a senior executive who has run political campaigns, or who has run cities, to battle the entrenched forces mustered by Kalanick’s dreaded taxi industry.

“Nobody likes him, he’s not a nice character, but he’s so woven into the political machinery and fabric that a lot of people owe him favors,” said Kalanick about the adversary such an Uber exec would be up against. “We have to bring out the truth about how dark and dangerous and evil the taxi side is.”

As it turns out, the pugnacious Uber leader was not kidding. He has taken the lead in talking to a series of high-profile political operatives over the last months to take over perhaps the most important position at the company right now as it battles cities like Miami, Austin and Las Vegas to enter those markets.

That includes, perhaps most interestingly, well-known Democratic strategist Howard Wolfson, who sources said has been perhaps the candidate who has gotten furthest along in the job search.

According to several people with knowledge of the situation, the talks between Wolfson and Kalanick — who apparently had developed a good rapport — are over, in part due to Wolfson’s need to stay in New York, where his wife holds a major new job at the Clinton Foundation.

But the aim at someone like Wolfson is interesting nonetheless, since he is a very heavy-duty political player. Most recently, he worked for former mayor of New York City Michael Bloomberg, replacing Kevin Sheekey as deputy mayor for governmental affairs. The move to Bloomberg was unusual since Wolfson — who appears all over cable shows and is a regular blogger — was the co-chief strategist and communications director for Hillary Clinton’s 2008 presidential campaign.

His wife, Terri McCullough, was chief of staff to former House Speaker Nancy Pelosi and has been director of “No Ceilings: The Full Participation Project,” a major women’s effort spearheaded by Hillary and Chelsea Clinton, since January.

Kalanick is still looking, having talked to other political players such as former Obama White House press secretary Jay Carney (whose name is also being bandied about for the other big job opening in tech PR, at Apple). In addition, said sources, Uber is looking at big corporate names.

While he is not listening to me in any way, there are lots of other names that would fit, including the well-connected Sheekey (who doesn’t know Kevin?) and perhaps Google’s top comms exec, Rachel Whetstone (who doesn’t know Rachel?). The idea, said sources, is to get someone in the mode of Facebook comms and public policy head Elliot Schrage, but stepping up the volume to 11.

Which, for anyone who knows Elliot, would be very loud indeed.

Uber has already made a move in this direction with the recent hiring of Ashwini Chhabra, who was deputy commissioner for policy and planning at New York City’s Taxi and Limousine Commission. He is now in charge of policy development and community engagement at the company.

In addition — like Airbnb, another company with regulatory challenges — Uber has hired a number of top lobbying firms in various cities it has been moving into.

The move to get a top PR honcho is in keeping with Uber’s recruitment of top-level execs for other key jobs.

That has included over the last year an impressive lineup, including former Googler Brent Callinicos as CFO; Emil Michael, formerly COO of Klout, as SVP of business; longtime Amazon exec Jeff Holden as chief product officer; and Ed Baker, who previously ran international growth at Facebook, as head of growth.

“Kalanick needs a counselor, a manager and an executor of his intention to grow everywhere,” said one person close to the situation. “The person he picks will say a lot about Uber’s future.”

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