New Amazon CEO Andy Jassy. Picture: BLOOMBERG/DAVID PAUL
New Amazon CEO Andy Jassy. Picture: BLOOMBERG/DAVID PAUL

Andy Jassy usually starts his keynote at Amazon.com’s cloud-computing trade show with what amounts to a tedious infomercial for corporate software.

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 succeeded Jeff Bezos as Amazon’s CEO 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.

Known for piercing questions that cut to the heart of the matter, he has a formidable radar for subordinates’ hyperbole

Bezos isn’t going away entirely. He will remain executive chair of Amazon’s board and plans to stay involved in 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.

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 worldwide who are probing whether big US tech companies have become too powerful. And he will 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.

It is unclear what Jassy might do differently in the CEO’s chair and, aside from endorsing Amazon’s preference for invention and big bets, he has been publicly quiet about his priorities.

Interviews with current and former colleagues, partners and competitors suggest he will 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.

Sportscaster career

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. 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. He later worked for a collectibles company and cofounded a short-lived start-up, before returning to Harvard for business school.

Cast, then Amazon’s marketing chief, spotted his CV 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 about another year 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.

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.

Most promising

“You just do these experiments, and he was always, always, always working on experiments,” designer Peter 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.”

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 daily, 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 and came to trust him implicitly.

“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.’”

At about this time, Amazon was starting to reorganise 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 co-ordinate 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 hi-tech rival such as Microsoft or Google spied the opportunity. Amazon Web Services launched its first major offerings three years later.

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

AWS signs and logos have become ubiquitous in the US. Picture: BLOOMBERG/CHRISTOPHE MORIN
AWS signs and logos have become ubiquitous in the US. Picture: BLOOMBERG/CHRISTOPHE MORIN

“We paid a lot of attention to our competitors,” a former AWS manager said. “They had these built-in advantages that we didn’t have. 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 centres in favour of the company’s services.

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 is more than double the market share of second-placed Microsoft. Jassy typically goes over those stats during his speech at the annual re:Invent customer conference. In the past 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 spokesperson 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. Criticism can be searing, but Jassy doesn’t make it personal, current and former colleagues say.

He gives teams wide latitude to steer their own course, but before being named Amazon’s CEO-in-waiting, remained heavily involved in day-to-day operations at AWS.

And he is copied on e-mails about service disruptions — each one an unacceptable failure — and occasionally drops into employees’ inboxes to make sure they have 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 is 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.”

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 929m² home, complete with a tennis court and a porch framed by towering Corinthian columns. The house sits in a central Seattle neighbourhood that is walking distance from a strip of bars and restaurants, which have become occasional venues for late-night meetings.

After homelessness became an all-consuming civic issue in Seattle, one Amazon was accused of worsening, Jassy joined a city council member on a one-night count to assess the scope of the crisis. The now-former council member, 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. 

A union rally in Bessemer, Alabama. Grappling with labour unrest is one of Jassy’s key challenges as part of his new role. Picture: BLOOMBERG
A union rally in Bessemer, Alabama. Grappling with labour unrest is one of Jassy’s key challenges as part of his new role. Picture: BLOOMBERG

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

Jassy himself is quite wealthy — he is worth about $500m, according to the Bloomberg Billionaires Index — but he is an unknown quantity outside technology circles.

Jassy’s work with AWS, a business he steered from 57 employees to tens of thousands and annual revenue of more than $50bn, 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 learnt one thing from Bezos, it is to take the long view. Amazon faces European inquiries into how it uses seller data, proposed legislation in the US 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 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 road map 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.

Bloomberg News. More stories like this are available at bloomberg.com.

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