Making Jack Dorsey CEO Of Twitter And Square Isn’t That Crazy

Serving as CEO of two companies is daunting, but Jack Dorsey is hardly the first to try it.

Making Jack Dorsey CEO Of Twitter And Square Isn’t That Crazy
[Source photo: Flickr user cellanr]

On Monday, Twitter formalized what had been the status quo since late July: The company’s cofounder Jack Dorsey would stay on as CEO, without giving up the CEO title of his payment processing company Square.


For most of us, the responsibilities of leading one company would be stressful enough, let alone two, especially two companies with the size, scope and high profile as Twitter and Square. Add to that stress the challenges each company currently faces, with Twitter’s growth slowing down and Square prepping for an initial public offering. Such a dual-CEO role is not inconceivable, though, because a lot of people have done it, including Howard Hughes, Steve Jobs, Carlos Ghosn (of Renault and Nissan), and Brian Lee (of ShoeDazzle and The Honest Co.).

Add in people who juggle multiple careers such as entertainer and entrepreneurs like Jay Z, as well as artists who write, direct, and star in their own movies or plays, and you have many more examples of people who manage multiple enterprises. Then throw in presidents and prime ministers. U.S. domestic policy is about a $2.8 trillion/year enterprise, and the military runs about $620 billion per year. (Then there’s job of running a continual political campaign.) That’s not to say most people have the temperament to be a dual, or even single, CEO; but those people do exist.

There’s not even a single management style that’s required for serving multiple roles. Steve Jobs was extremely hands-on–not just overseeing every design detail of Apple’s category-changing products but occasionally answering customer emails. (“Just avoid holding it that way,” he told a new iPhone 4 owner who was experiencing dropped calls from inadvertently covering the phone’s antenna). Howard Hughes directed his own films and designed his own planes; and Elon Musk designs cars and rockets. Brian Lee, in comparison, describes himself as “not that detailed” in managing his two companies. “I’m less involved and hands-on,” he said in an interview for PandoDaily in May 2013.

It Takes A Team

What all these polymaths do have in common is that they aren’t doing it alone–far from it. “The most important thing…it’s the people,” said Lee in the interview. Dorsey announced former revenue chief Adam Bain’s appointment as Twitter COO in the same tweet that announced his own as CEO. His next tweet said, “I have the smartest, strongest, and most determined leaders in the world on my teams.”


Adam Bain and Twitter’s CFO Anthony Noto were both candidates for the CEO position, according to a report in Re/code. That means each of them could probably handle the job of CEO, and they can pick up some slack for Dorsey.

At Square, Dorsey can lean on colleagues like chief financial officer Sarah Friar (formerly of Salesforce and Goldman Sachs) and former Google VP Françoise Brougher, now Square’s business lead.

The best CEOs are the ones who build the management capacity that allows the company to run without them. Despite the perception that Apple’s fate was inextricably linked to that of Steve Jobs, the company has continued to thrive since his untimely departure. It’s grown to be the most valued company in the world (although that has taken a hit) and is entering new categories with the Apple Watch and likely some type of automotive product on the way. It may take Tim Cook, Eddie Cue, Craig Federighi, and Phil Schiller to even approach the presence that Steve Jobs alone brought to a keynote event, but all together, they get through it.

A Focused Mission

Having a strong team lets a CEO go deep in a few key areas rather than futilely trying to stretch him-or herself across all the roles in the formal job description. Going deep is required, because the top dual CEOs generally don’t coast along with two stable companies. They help create businesses from scratch, rescue others from crisis, or both. Steve Jobs’s founding of Pixar and complete remake of Apple are well-known feats of management, but are not singular accomplishments.

With Tesla, Elon Musk is building an electric car industry that didn’t exist in any viable form previously; meanwhile, SpaceX rockets occasionally explode. He has a lot of challenges to deal with. Renault executive Carlos Ghosn took on the CEO position at carmaker Nissan in 1999 when the company had just lost $6.1 billion. A year later, it made a $2.7 billion profit. Ghosn didn’t perform magic; he performed surgery–cutting tens of thousands of jobs and whole divisions of the company.

Is Jack Dorsey The Next Steve Jobs?

Comparisons to Apple and Steve Jobs may be overused, but they are relevant in the case of Jack Dorsey. Both were ousted from the company they founded, both went on to found an innovative new company in a different segment of the tech industry, and both were brought back when the original company was faltering. If the comparison is to continue, Dorsey will have to be merciless, like Jobs (and Ghosn) in cutting out what needs to go.


Twitter’s revenue is strong and growing, but its user base is flattening out (though more than 300 million ain’t bad). That won’t change unless Dorsey and team can make Twitter less intimidating for newbies. The first people on Twitter were power users wiling to figure out handles, hashtags, retweets, and how to build up a proper roster of followers and an interesting list of people to follow. In fact, those early users co-invented many of Twitter’s features–the same ones that are baffling to newcomers not steeped in Twitter’s origins.

Dorsey seems solidly focused on the usability problem. In his first earnings call as interim CEO on July 28, he was brutally honest. “Product initiatives we’ve mentioned in previous earnings calls…have not yet had meaningful impact on growing our audience or participation,” Dorsey said. “This is unacceptable, and we’re not happy about it.” Noto chimed in saying, “The product remains too difficult to use. We need to simplify the product so everyone can get value from Twitter faster.”

Despite being a cofounder, Dorsey doesn’t seem to consider any aspect of Twitter–even its core elements–to be beyond scrutiny: not the reverse chronology timeline, not even the defining 140-character limit. He has spoken passionately and frequently about Project Lightning, a more curated Twitter experience, which launched today as Moments.

Not all CEOs have to, or even can, dedicate their energies to working through the details of product design. But when a company is in crisis, sometimes only the CEO–especially one who’s also a founder–has the clout to push through the kind of radical pruning and fixing that the company needs to survive. We’ll see in the coming months if Jack Dorsey is one of the people who can pull that off.


About the author

Sean Captain is a Bay Area technology, science, and policy journalist. @seancaptain.