What tech insiders really think of Andy Jassy, the soon-to-be CEO of Amazon 

Once a week, Andy Jassy calls a meeting to track performance at Amazon Web Services (AWS), the retail giant’s cloud computing arm which Jassy has led since the early 2000s. In the meeting the 53-year-old grills each team on its achievements. “He has very high standards,” says someone familiar with the event. “You need to know what you’re going to present and be ready for him to dive really deep into the details and pick apart what you’re saying.”

But as AWS grew, so did the meeting’s agenda and there were concerns that some employees weren’t doing their homework. To keep everyone on their toes, Jassy created a handmade Wheel of Fortune which he would spin. If the arrow landed on an individual’s section they would be asked to stand and present to the whole group.

Just the thought makes the palms sweat, but it’s clearly a winning formula for the man Jeff Bezos has tasked with taking the reins of his $1.7 trillion company when he steps back later this year. 

But who is Andy Jassy, the soon-to-be CEO of Amazon? 

“He’s the most powerful person in tech that nobody has ever heard of,” an insider told me when I first arrived in Silicon Valley two years ago. As the leader of AWS, a $45.4 billion branch of Amazon that offers on-demand IT resources such as storage and databases to millions of internet companies on a pay-as-you-go basis, he is responsible for the basic building blocks that make up a huge chunk of the internet. In 2020 Jassy’s division was responsible for 63% of Amazon’s overall profits.

As a British newbie in tech circles, cloud computing was an enigma. Little did I know that the likes of Netflix, Nasa, Facebook, Spotify, the BBC and Airbnb all depend on AWS’s services to function. “AWS powers our whole life," said a friend in tech. “And Andy Jassy powers AWS.”

Raised in Scarsdale, a small town just north of New York City, Jassy graduated from Harvard in 1990 with aspirations to become a sports commentator. He worked briefly for NBC, ABC and Fox News before realising that, “I didn’t have the patience to put in all the years before you really get a shot”. Instead he joined Harvard Business School and landed a job at Amazon in his final year. “I took my last final exam at HBS, the first Friday of May in 1997 and I started Amazon the next Monday,”  he revealed in a podcast interview in September. That was three weeks before the online book seller went public.

He and his new wife, Elana Caplan, a fashion designer, decided to relocate to the West Coast for just a few years before returning to New York. “That was kind of the agreement we made on the napkin of a bar when we made our decision [to move],” Jassy says. “And that was 23 years ago.”

Bezos quickly saw the young entrepreneur’s potential and made him his ‘Shadow’, a chief-of-staff role which involved following the founder around for 18 months. “I thought that I had very high standards before I started that job,” Jassy continued. “And then… I realised that my standards weren't high enough.”

His Wheel of Fortune tactics suggest he has upped his game. One former staff member also described him as “a shark who will smell a drop of blood from 100 miles away if you're not ready.”

Yet this is where the cut-throat analogies end. 

“Gracious”, “empathetic” and “humble” are some of the words former staff members and mentees have used to describe him to me this week. 

When AWS moved into a new skyscraper in Seattle, he named one of his two conference rooms Rothschild after a teacher he admired in high school. The other is called The Chop, not because it’s where people get fired, but after a book he read in college called The Charterhouse of Palma. Apparently Jassy didn’t even like the story but called his old dorm room The Chop, because he thought the name sounded ‘awesome’. A huge music and film fan he has posters of rock bands up in the office and until recently owned thousands of CDs. When he likes something he says, “giddy up, let’s get going,” and replies to the majority of his emails with a simple ‘nice’.

“He’s the kind of person you’d like to sit down and have a beer with,” a current employee tells me over the phone. 

By all accounts, you will need a beer to wash down all the chicken you’ll be consuming. In his Twitter bio Jassy describes himself as ‘an experienced buffalo wing eater’, a reference to a chicken wing-eating club he started at business school and established at AWS. It was even incorporated into the company’s annual conference in Las Vegas where 60,000 attendees broke the Guinness World Record for the largest ever chicken wing eating competition.

Apparently Jassy’s personal record is more than 50 in one sitting.

“He’s very down-to-earth” agreed a friend of mine who sat on a round-table discussion with the businessman at Davos. “He was clearly the most important person in the room but you would never guess.”

As elite executives go, Jassy is certainly understated. He’s known in tech circles for flying economy to work events, spent years driving a 1990s Jeep Cherokee and still uses a Blackberry phone, much to the amusement of his team. He prefers to read documents in print, wears bog-standard Converse trainers and has been accused of only owning a handful of flannel shirts which he rotates throughout the week (although I’ve been told that he now dons a suit jacket for important meetings).

A number of tech workers I know were surprised that Jassy’s net worth was ‘only’ $440 million. “I thought it was a typo when I read it,” one confessed. “On the grand scale of Amazonians that’s not very rich” another told me. Indeed, it pales in comparison to Jeff Bezos’s $184 billion.

Even Jassy’s two houses - one in Seattle which he bought for $3.1 million in 2009 and a more recent $6.7 million Santa Monica residence - are modest by tech tycoon standards. Bezos owns six properties in the US alone including the world’s most expensive home (the $168 million Jack Warner Estate in Beverly Hills) and a former Washington museum with 25 bathrooms, five living-rooms and two libraries. The only newsworthy element to Jassy’s home in Seattle is a basement sports bar decorated with ticket stubs from the Super Bowl.

“I think this [transition] will be a similar situation to Steve Jobs handing over to Tim Cook at Apple” says Jon Reily, a former Amazon executive who worked with Bezos from 2011 to 2015. “Cook came in with a CFO mindset. He wanted to know the nuts and bolts of everything. And Steve Jobs just wanted the high points so that he could sell it,” Reily says.

Jassy does seem to lack the shine of Bezos, who before Covid-19 was hosting star-studded soirées and wearing matching pinstripes with his girlfriend Lauren Sanchez at Wimbledon. But Reily says this is a new side to the Amazon founder. “Jeff also used to be a down-to-earth guy. Hollywood changed him.” 

Could the same happen to Andy Jassy? Not according to insiders who feel confident that their boss won’t be sidetracked by fame, fortune and flying to the moon.

That’s a relief because soon he’ll be the most powerful person in tech that everybody has ever heard of.

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