On a fall day in 2010, Jack Dorsey stepped before his staff at Square, his payments startup, to deliver a pep talk at its weekly all-hands meeting. He was dressed in a rakish dark Prada suit and tie that was much more Don Draper than Silicon Valley wunderkind. Just two years earlier, Dorsey had been ousted from his CEO role at Twitter, where he failed to delegate effectively, motivate sufficiently or inspire trust in his leadership. Now, he appeared to be a transformed man, not only in appearance, but in vision.
Dorsey waxed on about the Golden Gate Bridge — its flawless design, its remarkable engineering and its unwavering utility. He contrasted it with the pedestrian Bay Bridge and its narrow lanes — an eyesore compared with its more charming neighbor.
"A lot of people in our industry, this is what they're building," he said. "It's terrible."
"We want to design the beautiful," he said with a nod to the Golden Gate, "and build the impossible."
He then laid out in clear and confident terms, according to those who attended, what his role was in making sure that happened.
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"I think I'm just an editor, and I think every CEO is an editor," he told the room of about 30 executives, engineers and staffers. "I think every leader in any company is an editor. Taking all of these ideas and you're editing them down to one cohesive story. … We have all these inputs, we have all these places that we could go — all these things that we could do — but we need to present one cohesive story to the world."
Several former employees of Square point to that talk as the birth of a new Jack. Not a final version, but a coming-out party of sorts for a brilliant design and technical mind who was re-energized and ready to transform into a leader after a humiliating ouster from Twitter.
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Now Dorsey, at 38, finds himself leading not one but two big companies. He plans to remain CEO of Square, which is slated to go public this year even as he is expected to be named the CEO of Twitter, a role he has held on a temporary basis since June. What some think is crazy, Dorsey believes to be fulfilling.
"It's exhilarating for him," one long-time confidante said. "He draws energy from how to think about both companies."
Whether by coincidence or design, Dorsey's comeback closely resembles the Steve Jobs Narrative — a modern myth Silicon Valley entrepreneurs hold up as a map to absolution. Like the Apple co-founder, Dorsey was the impetuous, petulant CEO pushed out by his allies. And after a soul-searching exile, he's welcomed back as the savior to a troubled enterprise. Even his line that every CEO is an editor is said to have been borrowed from Jobs.
What's so different about Dorsey now?
This time, the bitterness that marked his brief return to Twitter in 2011 as executive chairman and product czar appears to be gone. This time, he comes with the pedigree of having built from scratch a company — Square — that is on the precipice of an IPO. This time, according to more than 20 current and former colleagues Re/code interviewed over the past few weeks, Dorsey has grown up.
The Makeover
From the start at Square, Dorsey was intent on smoothing over some of his rough edges, and perception, he learned, was everything.
In his first stint at Twitter, Dorsey would piss off some employees when he would leave ahead of them at night for yoga or drawing lessons, according to Nick Bilton's book "Hatching Twitter." Dorsey supposedly got back to work later at night, but people didn't know that. So at Square, Dorsey made a point of arriving early and staying late, especially when his employees were grinding away into the evening.
"He realized if it's perception, it becomes reality," a former employee said. "So he made sure the perception changed."
Also gone were the nose ring, the casual jeans and white T-shirts he rocked while at Twitter, replaced by sleek suits from Hermes and Prada. No one in Silicon Valley wore suits.
Some things changed slowly. Dorsey would become engrossed in a particular project and obsess over the smallest details, frustrating employees. These days, he picks his obsessions more carefully.
But over the next few months, Dorsey did something even his most fervent supporters weren't sure he had in him: He hired superstars and then delegated immensely.
And while he edited out some faults, others crept into his repertoire. When Dorsey saw star potential in a new employee, he pulled them into his inner circle quickly and rewarded them with a ton of responsibility. Such confidence can serve to build up young employees and inspire them to accomplish things they wouldn't have otherwise even attempted. But in several cases, the moves backfired, multiple sources said.
"It made people feel like Jack had a revolving door of his favorite people," one former employee during this time said. "They would say, 'You're Jack's favorite now, but it could change tomorrow.'"
And it did. Dorsey set expectations so high, and made them so widely known, that there was sometimes nowhere for these people to go but down. At least two of his one-time favorites left Square within a year of joining.
Over time, Dorsey has learned from these episodes, sources said, and has been helped by the recruitment of a team of senior leaders who sit between him and most divisions of the 1,200-person company. Twitter, Square and Dorsey declined to comment for this article.
In some respects, Dorsey was backed into this position. In 2013, he faced one of his biggest crises at his new company when the COO, Keith Rabois, left following a sexual harassment claim from a co-worker. Rabois denied any wrongdoing and Square backed him on it, but he had become a distraction and was asked to leave the company despite how much Dorsey had relied on him. Rabois was seen as Dorsey's right-hand man, and many wondered how Dorsey would cope with the loss of someone who many viewed as the company's day-to-day operator.
But over the next few months, Dorsey did something even his most fervent supporters weren't sure he had in him: He hired superstars and then delegated immensely. He snagged Francoise Brougher, an under-the-radar but high-powered executive at Google, to build a sales team and push new revenue-generating products into market, and Gokul Rajaram, a highly respected Facebook product boss.
A year later he would add Alyssa Henry, from Amazon's AWS, and eventually handed over all product and engineering to her for the core merchant products business. Add that group to existing execs like CFO Sarah Friar, a former analyst with Goldman Sachs, and hardware boss Jesse Dorogusker. Suddenly, Dorsey had assembled perhaps Silicon Valley's deepest bench at a private company.
Hiring a top team — and trusting them — has had other benefits. It has given Dorsey time to burnish a reputation as a big thinker — the person who can predict a trend from 30,000 feet.
Whether intentional or otherwise, this approach freed him up to spend more time on the projects at Square that he was most passionate about — like the money-transfer service, Square Cash, and a new version of Square's flagship credit card reader that works with the chip credit cards that are becoming mainstream in the U.S.
In recent months, this structure has also allowed him to spend significant time at Twitter, even as Square has filed confidentially to go public. Execution, it's now clear, no longer halts when Dorsey is away from Square's office.
Dorsey has also learned to stop dallying too long on favorite projects that don't work, an issue that plagued Twitter during his time leading product in 2011. Square Wallet, Dorsey's dream to transform the way shoppers pay for stuff in stores by telling cashiers their names, never took off because there wasn't a good enough reason to use it instead of more traditional payment methods. A partnership with Starbucks also failed to distribute the technology as widely as Square executives had hoped. But it lived on for a few more years because it was Jack's baby.
When it was clear that Square Wallet's next incarnation, Square Order, an app that let people order things like coffee for pickup, wasn't working, Dorsey and the team killed it within 10 months.
Although Dorsey has not given up on the consumer market, he has also come to the realization that Square is a company primarily focused on building products for business owners, not shoppers, sources said.
He still pushes people hard, but not to a breaking point. One of his favorite words is "Why?" which can flummox employees who haven't worked closely with him and make them think he instantly doesn't like an idea. He loves to debate and challenge the answer to the "Why?" even if he agrees with a decision; one Twitter employee described Dorsey as liking to stir the pot. And when he eventually gets you to come around to his thinking, he will — often with a smile — let you know that he was right.
Beyond the slick suits and the trendy haircuts, flashes of the old, more impulsive Jack still remain.
In the spring of 2014, a Wall Street Journal article about Square raised questions about its financial footing and set off a wave of negative stories about Square burning through tons of cash. At the time, Re/code reported that Square was not looking for a buyer — Apple and Google had sniffed around — and any talks did not move further.
By August, with bad press piling on, Dorsey had had enough. He pushed the company to publish a screed titled "Top 10 Myths About Square." The move backfired, setting off another wave of bad press.
And then suddenly, Dorsey left San Francisco the next day and was discovered on Twitter to be on the ground in Ferguson, Mo., near his hometown of St. Louis, where riots had broken out after the shooting by a white police officer of an unarmed black man. There was Dorsey, the billionaire CEO, marching with protestors and tweeting Vine videos along the way. Some employees were furious with his decision to skip town in a moment of crisis. But a surprising amount of the company was understanding, several insiders said. The feeling among his supporters was this was Jack doing what Jack thought was the right thing, no matter what anyone thought.
"A lot of people work at Square because they really believe in him and the ethics of the company," one long-time former employee said. "I can't say I joined Square because I wanted to save the world. But there are hundreds of people at Square right now who could be working anywhere, and they choose to stay because Jack is the kind of CEO who was tweeting from Ferguson."
The Return
Since June when Dorsey stepped back in to lead the company he co-founded, he has owned the role despite the "interim" in his title. There is no single explanation for why Dorsey's current run at Twitter feels like the real deal, but it does. Insiders are swept by the way he talks about the product. Dorsey emails frequently with the entire staff, sometimes multiple times a day to talk about what he loves about Twitter and where he sees things going.
He seems to be a completely different man than the one who returned to Twitter in March 2011 as executive chairman and product czar. Former colleagues recall a man looking for payback for his 2008 ouster; loyalty was key, and many who were loyal to Twitter's other co-founder, Ev Williams, were booted from the company. Back then, Dorsey would routinely sit in on meetings without saying a word. When he did speak, his contributions were so abstract that few understood what he was talking about. In some cases, he'd simply write a single word or two up on the whiteboard.
He no longer sits silently in meetings — current colleagues say he provides the kind of direct, constructive feedback you'd expect from someone with Dorsey's reputation as a product guru. There's still some fear that Dorsey will send people packing, but the chip on his shoulder appears to be gone. Even Twitter co-founder and good friend Biz Stone said something has changed with his friend in the last few years at Square.
"I feel like he went into a time chamber and studied for 40 years and came out after one," Stone said. "It's like, what happened? Where did you get all this confidence and great answers and specificity? He seems to be much deeper now. It's like talking to a much older person."
Beyond new communications skills, the new Jack Dorsey has also demonstrated a willingness to make big shot calls. People within the company have discussed the idea of tweaking how Twitter measures its 140-character limit by removing things like links and user handles from the count, according to sources, a discussion that has been ongoing for years but has resurfaced in recent months. (Dorsey is a supporter.) He even signed off on a separate project that would allow Twitter users to publish content longer than 140 characters, either in a tweet itself or appended to it in some way.
Taken together, these moves, which may appear subtle to outsiders, symbolize a radical departure for a company born a year before the launch of the first iPhone and in an era when text messaging was the dominant form of communication. It's clear Dorsey is not tied to the company's legacies, even one as sacred as Twitter's 140-character limit. Many insiders believe that only someone with the confidence of a founder could make these decisions to break from the past.
Dorsey is already acting the part in other ways, too. He restructured Twitter's product team just two months into his new role, promoting former Crashlytics CEO Jeff Seibert to ensure there was someone responsible for the core product day in and day out. Ownership over projects has been an issue at Twitter in the past. The company has more than 4,000 people and some believe it has grown too fast. Insiders say that it isn't always clear who is responsible for what. At times, it can feel scattered, like there's a lack of focus.
"Twitter had a massive lack of accountability or decision-making structure under the CEO level," according to one insider.
Dorsey has brought with him a sense of urgency as well, giving Seibert a matter of weeks to decide which 10 product ideas Twitter will pursue and which will be shelved. "He loves constraints," a source said. "He loves the creativity and thinking and simplicity that comes out of it."
Challenges
Juggling two gigs didn't work out so well for Dorsey the first time around in 2011. At the time, Dorsey was splitting time between Twitter and Square, which had just launched its first major product. He was also overseeing Twitter's major redesign known as T1 that introduced the Discover tab. It wasn't seen as a success. His role within Twitter ultimately didn't work, and he left in late 2012 to focus on Square full-time. "[T]he pace was exhausting, and he alienated some Twitter employees," is how a 2013 New Yorker profile put it.
This time, the stakes are even higher. Twitter is clearly in danger. Since going public in 2012, it has suffered numerous executive shuffles and stagnant user growth while its stock has fallen 40 percent from its close on IPO day. That's why Twitter's board once demanded that whoever took over would need to do so full-time.
Meanwhile, Square is gearing up to go public, and Dorsey will soon be on the road, leading Square's IPO roadshow, a potentially multi-week process where he will need to convince big-money investors to back a company in a notoriously tough sector that faces formidable, well-financed foes, including Amazon.
The good news for investors is that our sources — and we mean almost all of them — believe that if anyone can run these two companies, it's Dorsey.
He has always been meticulous about his schedule, and that has not changed in the last three months. Dorsey has a routine: mornings are spent at Twitter, afternoons at Square, and frequent stops at Blue Bottle are sprinkled in between, a small coffee shop nestled between Twitter's two lofty office buildings on 10th Street in San Francisco, less than 500 yards from Square's headquarters just down the block.
The proximity certainly helps, but it's Dorsey's skill set that gives most colleagues confidence he can do the job. Twitter has long struggled with user growth and adoption, issues that many believe stem from two things: The product and the message. These are two areas where Dorsey thrives.
No one has been thinking about the Twitter product longer than Dorsey, current and former employees say. He has transformed into a skilled communicator of a vision for Twitter from a product and corporate perspective. He has shown an ability to construct a strong management team, which he will need to rely on as he splits his time between the companies.
Back in 2010, Dorsey told his employees at Square that every CEO is an editor. Now the world will soon see how the Jack Dorsey Narrative plays out.
—By Kurt Wagner and Jason Del Rey, Re/code.net.
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