How Andy Jassy raced to the top of Amazon

But last December, at an event held virtually rather than in a Las Vegas ballroom, the Amazon Web Services boss did something different: He talked about society. After acknowledging the tragedy of the coronavirus pandemic, Jassy called out the killings of three Black Americans that had sparked unprecedented protests across the country.

“The reality is for the last several hundred years, the way we treated Black people in this country is disgraceful and something that has to change,” he said.

Jassy, who succeeds Jeff Bezos as Amazon’s chief executive on July 5, is steeped in the company’s corporate religion: Put customers first, move fast, be frugal. He shares his boss’s competitive streak and mistrust of conventional wisdom.

But the 53-year-old executive is no Bezos clone. Known for piercing questions that cut to the heart of the matter, he has a formidable radar for subordinates’ hyperbole. At the same time, he is unassuming and connects easily with colleagues. Moreover, unlike the sometimes single-minded Bezos, Jassy has long engaged with society outside Amazon’s walls, as he showed by declaring unequivocally that Black lives matter.

Bezos isn’t going away entirely. He’ll remain executive chairman of Amazon’s board and plans to stay involved with the company’s new projects. Yet his decision to hitch a ride on his rocket company’s suborbital space flight just weeks after handing over control suggests Bezos won’t constantly be second-guessing Jassy, a deputy he’s long trusted to manage his own shop. 

It falls to Jassy to continue Amazon’s track record of invention, which extends from cloud-computing and smart speakers to the heavily automated warehouses that enable one-day shipping. He will dictate Amazon’s response to regulators around the world who are probing whether big U.S. tech companies have become too powerful. And he’ll have the task of seeing through Bezos’s recent pledge that the company will do better by employees, a declaration that follows a year of unrest in the company’s warehouses and, occasionally, at its Seattle headquarters. Days before Jassy’s ascension, the company updated its leadership principles, urging managers to lead with empathy and consider employee and societal welfare when making decisions.

It’s not clear what Jassy might do differently in the CEO’s chair and, aside from endorsing Amazon’s preference for invention and big bets, he’s been publicly quiet about his priorities. The company declined to make him available for this profile.

Interviews with current and former colleagues, partners and competitors suggest he’ll be as hard-charging as Bezos when pursuing new opportunities. “He will be just as ambitious and bold as Jeff has been, if not more so,” said Jennifer Cast, who hired Jassy at Amazon in 1997.

Obsessive music fan

Jassy grew up in the affluent New York suburb of Scarsdale, the middle of three children. His father led a prominent Manhattan law firm, and his mother was a homemaker. Dinner-table conversation frequently turned into debate about sports teams, teachers or favorite relatives.

“You never got away with telling a story without being interrupted constantly with questions about the details or decisions you made,” Jassy said in a 2018 commencement address. He could easily have been describing how Amazon employees feel sitting across from him in high-pressure meetings.

A skilled youth tennis player, Jassy also played soccer and considered himself a jock. He didn’t read outside of his studies. “School was a bit of a game to me,” he said in a speech at the Scarsdale school district booster club, where he credited a talented American history teacher with getting him to engage more with schoolwork.

After following his father to Harvard and earning a degree in government, Jassy moved to New York to pursue a career as a sportscaster. Stints at ABC Sports and Fox ended in frustration at the prospect of putting in years of work before getting a shot, impatience often found in the halls of Amazon. Jassy later worked for a collectibles company and co-founded a short-lived startup, before returning to Harvard for business school.

His then-fiancée, Elana Caplan, grew up in southern California, and Jassy said he would go out west after business school if she agreed to move back to New York after a few years. Jassy figured he was in the running for a job in San Francisco with tax preparation software maker Intuit when Cast, then Amazon’s marketing chief, spotted his resume in a pile from the business-school career office.

Jassy took his final exam on a Friday in May 1997 and joined Amazon in Seattle the next Monday, a week before the company’s initial public offering.

Posted to the tiny marketing department, Jassy was quickly drafted to explore what the company should sell after books. While two business-school classmates studied video and packaged software, Jassy wrote the plan for Amazon’s entrance into the music business.

An obsessive fan whose tastes span guitar-heavy rock, East Coast jam bands and singer-songwriters, Jassy was passed over to be the first leader of Amazon’s CD business. He was crushed and considered quitting, he later recalled.

After another year or so back in marketing, he made it to the music team, helping lead a ragtag group of MBAs, software engineers, former journalists and DJs. Working on an upper floor of a dingy brick building in downtown Seattle, the team often stayed late enough to feel the thumping bass from a club on the ground floor. Stale cigarette smoke from the bar still hung in the air when the Amazonians returned early the next morning.Jassy sometimes played CDs in the evenings as the team ate dinner at their desks.

Peter Hilgendorf, a designer who did three stints at Amazon, starting in the late 1990s, was on a ski trip near Vancouver, British Columbia, when he got a call from Jassy at about 6 a.m. Amazon was considering making an offer for Napster.

“He’s like, ‘can I get you to come into the office in a couple hours?’” Hilgendorf said. “I’m like, ‘I’m in Canada.’ He says, ‘OK, can you get here by noon?’”  

A Bezos edict holds that Amazonians must work long, hard and smart. Jassy embodied that from the beginning—and required it of those around him. A few members of the music team pulled an all-nighter to sketch out what an Amazon digital music business might look like if the company acquired the pioneering but ill-fated file-sharing service. Amazon disputes that description of events.

“You just do these experiments, and he was always, always, always working on experiments,” Hilgendorf said. Could Amazon get into concert tickets? Start a record label? “What’s the next thing? It had to be fast, and had to be meaningful.”

For many of the mostly young core of employees at Amazon, work and personal lives blended. Dave Schappell, hired by Jassy in 1998 to help build out Amazon’s music team, found himself hitching a ride with Andy and Elana Jassy, who were going toa Dave Matthews Band concert two hours east of Seattle at a legendary outdoor amphitheater. “I started on a Tuesday, and on Friday night he took me out to the Gorge,” Schappell said. “Literally, he didn’t know me.”

Shortly after the dot-com bust, Bezos asked Jassy to become his shadow—a temporary chief-of-staff-like posting awarded only to the most promising managers. For about 18 months, Jassy followed the boss around every day, sitting with him in meetings and serving as his ears in rooms where Bezos’s presence could throw discussions off track. Bezos was already a Jassy fan—even saving his job during a round of layoffs in the marketing department and dubbing him “one of our most high potential people,” according to a member of Bezos’s executive team. He came to trust Jassy implicitly. Unlike some executives who occasionally censored themselves to avoid confrontation with a temperamental CEO, Jassy told it to Bezos straight.

“He was someone who will tell you the truth,” said Ian Freed, a former Amazon executive who also worked as Bezos’s technical adviser. “He would say it in a thoughtful and respectful way: ‘Jeff, here’s what I saw in that meeting, and here’s why I think we should try it in a different way.’”

AWS is born

At about this time, Amazon was starting to reorganize its technology infrastructure. New initiatives were getting bogged down, and throwing more developers at the problem didn’t speed things up. Amazon decided to break apart cumbersome technology teams into smaller groups responsible for a single service or component. Instead of asking them to coordinate when pursuing new projects, they would set up their software so that others could tap into it without any additional effort.

Bezos and his deputies, prescient in foreseeing the internet’s disruptive power in retail, figured a similar revolution might also be coming to computing. In 2003, Jassy left the shadow job to outline how such a business might work and, when the board approved his proposal, bring it to market before a high-tech rival like Microsoft or Google spied the opportunity. Amazon Web Services launched its first major offerings three years later.

Their best customers at first were technology startups, companies not already committed to mainframe computers or backroom servers. Amazon’s pay-for-what-you-use model eliminated the sticker shock of buying a new set of servers, offering upstarts like Airbnb a way to use the latest technology and only add resources as it needed them.

Corporate technology giants were slow to recognize the threat, puzzling Jassy and other executives in Seattle.

“We paid a lot of attention to our competitors. They gotta be coming for us at some point,” a former AWS manager said. “They had these built-in advantages that we didn’t have. So we’re always paranoid. We’d better be running like hell to stay far ahead, because being ahead is the only advantage we have.”

How far ahead the world didn’t know because Bezos and Jassy had AWS’s sales buried in Amazon’s financial results until 2015. By then, big companies were unplugging data centers in favor of the company’s services.

Like Microsoft in the heyday of the personal computer, AWS staked its claim as the leader in a new era of computing. And like Microsoft, AWS has been accused of being hypercompetitive, whether rolling out products that trample those of partners, or seeking to commercialize open-source projects built by others. Amazon’s view, employees say, is that if AWS engineers think they can solve a problem affecting enough customers, they should do it. “Amazon is focused on building and inventing on behalf of customers who use AWS and shop in our store,” a company spokesman said in an email.

In 2020, according to Gartner, Amazon held almost 41% of the market for cloud-computing infrastructure services, the foundational building blocks companies use to build software and run their systems. That’s more than double the market share of  second-place Microsoft. Jassy typically goes over those stats during his speech at the annual re:Invent customer conference. In the last two years that portion of the presentation was nixed from recorded versions, prompting some attendees to wonder if the growing antitrust pressure on Amazon was a factor. A company spokesman said Amazon removed the data before posting the videos because of licensing restrictions.

Jassy, who worked with Bezos and other executives to craft Amazon’s guiding principles, followed them to the letter in setting up AWS’s writing- and data-driven culture. Employees present ideas as short, written narratives. Life at AWS is punctuated by weekly operational and product reviews with the boss. Jassy’s questions tend to come last, and his interrogation often identifies weak spots in a proposal or assumptions presenters hadn’t fully thought through. Criticism can be searing, but Jassy doesn’t make it personal, current and former colleagues say.

Projects are assigned to small, largely self-directed teams, and Jassy relishes pushing for impossible-seeming deadlines. Burnout is common. A frequent question that bounces around AWS comes from Jassy: What would it take to make what you’re working on 10 times its size?

“It was absolutely a sprint,” said Peter Sirota, an early AWS product manager. “A continuous sprint.”

To rally the troops, Jassy begins and ends meetings by thanking his teams, uncommon niceties at a company full of confrontational, Type-A personalities. Many Amazonians have stories of moments when Jassy sought to connect with them on a personal level, often using his encyclopedic knowledge of sports, music and indie movies to find common ground. While Bezos can go through meetings without showing much interest in the underlings sitting around the table, Jassy is more likely to strike up small talk with product managers waiting to present.

He likes silly games that bring out his team’s competitive urge. During his days on the music team, Jassy’s office hosted a game called “The Ledge,” where challengers had three chances to throw and land a dry erase marker on the white board. “You’d hear people screaming,” said Cast, who was his supervisor on the music team. “He’s just very, very competitive.”

Jassy never fell out of love with New York sports teams, particularly the Rangers and Giants, and owns a minority stake in the Seattle Kraken expansion hockey franchise. Jassy has friends and coworkers over to watch games in his basement bar, runs basketball pools and fantasy football leagues. For years he has sponsored an Amazon chicken-wing eating contest, a version of which is now featured at AWS’s customer conference.

He gives teams wide latitude to steer their own course, but prior to being named Amazon’s CEO-in-waiting, remained heavily involved in day-to-day operations at AWS. He edits press releases and marketing materials, helps name products and has strong opinions on where to set prices. He monitors Twitter. 

And he’s copied on emails about service disruptions—each one an unacceptable failure—and occasionally drops into employees’ inboxes to make sure they’ve seen the problem. The only appropriate response is that the team is already working on a resolution. Some employees say seeking Jassy’s approval can be a bottleneck. Teams spend weeks or months debating and editing documents to get them “Andy-ready.” Some at Amazon worry that such an approach would fail if he seeks to replicate it in steering the entire company.

Three people who have worked closely with Jassy say he’s behind AWS’s threats and non-compete lawsuits against employees who leave for rivals. Amazon denies this. The  litigious pattern recently fell on Brian Hall, a marketing executive who decamped for Google and whose case was settled confidentially.

“That’s Andy feeling a betrayal,” one of the people said of the lawsuits. “I’m going to come after you with everything I’ve got. It’s as much for the folks that remain as the folks that leave.”

As AWS grew, Jassy replaced elements of his flannel-heavy uniform for a rotation of checkered button-down shirts, typically paired with jeans and sneakers. He lost weight, starting his days with an hour on an elliptical machine at his home gym, ESPN on in the background as he reviews documents brought home the night before. He switched from Diet Coke—cans of which he once chucked indiscriminately in the back of his 1990s Jeep Cherokee—to bottled water. Bezos, who in recent years has swelled into an action figure in tailored shirts, is handing the reins to a slightly rumpled and frugally dressed executive.  

Urban roots

Whether speaking at Amazon or in public, Jassy is disciplined, echoing Bezos’s paeans to customers. Colleagues say he has a near-photographic memory and easy fluency with data and technical topics despite a lack of formal training as an engineer.

Many executives in Seattle’s booming technology sector live on lakeside compounds in the suburbs. The Jassys opted to put down urban roots, in 2009 buying a 10,000-square-foot home, complete with a tennis court and a porch framed by towering Corinthian columns. The house sits in a central Seattle neighborhood that’s walking distance from a strip of bars and restaurants, which have become occasional venues for late-night meetings. Known for responding to email at all hours, Jassy is also diligent in setting aside time for his family, excusing himself from some meetings that run into the evening and holding time in the mornings for standing breakfasts or tennis matches with his kids, now aged 20 and 17.

After homelessness became an all-consuming civic issue in Seattle, one Amazon was accused of exacerbating, Jassy joined a city council member on a one-night count to assess the scope of the crisis. The now-former councilmember, Sally Bagshaw, had no idea that guy who introduced himself as Andy from Amazon was a big deal until she noticed his security detail trailing them from a respectful distance. 

Friends and coworkers say they detect in Jassy none of Bezos’s libertarian leanings, though he studiously avoids partisan political commentary at work. Elana Jassy has donated to Democratic candidates and committees in recent years.

Perhaps the biggest immediate change he brings to the CEO role is cosmetic. Bezos, the world’s richest man, owns lavish homes across the U.S., a rocket company and the Washington Post, cutting the figure of a cartoon plutocrat. He is a go-to target for income-inequality critics, anti-monopoly scholars and labor unions.

Jassy himself is quite wealthy—he’s worth roughly $500 million, according to the Bloomberg Billionaires Index—but he’s an unknown quantity outside technology circles, giving Amazon an opportunity to introduce him to the public.

Jassy’s work with AWS, a business he steered from 57 employees to tens of thousands and annual revenue of more than $50 billion, is already the subject of reverent business-school case studies. But while Bezos is an idea-a-minute machine whose musings led to the Alexa digital assistant and cashierless Amazon Go stores, Jassy is better known as a facilitator of creative thinking in others.

If Jassy has learned one thing from Bezos, it’s to take the long view. Amazon faces European inquiries into how it uses seller data, proposed legislation in the U.S. that would force the company to cleave its logistics business from its retail website and a District of Columbia antitrust lawsuit alleging it raised prices on customers. These inquiries are expected to take years to resolve, so Amazon has time to tinker with its response.

So far, the company seems bent on a more aggressive posture, sparring with critical members of Congress and marshalling Amazon’s public-policy arm to portray the e-commerce giant as a friend to small business. Jassy’s legacy will rest not just on continuing to add loyal Prime members and increase AWS’s share of technology spending, but on how he leads Amazon through its antitrust entanglements and moment of cultural reckoning. The roadmap, in other words, is not just to fix what ails customers, as Bezos did profitably for so many years, but to demonstrate that Amazon is ready to be a good corporate citizen.

At Amazon’s cloud conference last December, Jassy said Amazon would do its part to address systemic racism, a commitment he reinforced months later after a Black AWS employee sued the company, claiming racial and gender discrimination.

“We’re working on it at Amazon, I know a lot of companies are,” Jassy said. “It’s going to take several years of us working together, but we need to do it.”