As Jeff Bezos Takes Off, Meet His Earthbound Successor

Who, you might ask at this moment, is Andy Jassy?

He’s a talented entrepreneur, for sure, having built Amazon Web Services from a skunkworks inside a larger company starting in 2006 to one of the most valuable entities in the world.

He’s been controversial, too, leading the development of AWS’ Rekognition facial recognition software and vociferously defending it when law enforcement has been accused of misusing it.

Mr. Jassy has been diplomatic, making sure that AWS has largely avoided the crises that have ensnared other digital entities nested inside Amazon, despite the glare of scrutiny from both regulators and advocacy groups, including when it recently kicked Parler, the right-leaning social network, off its platform in the wake of the Jan. 6 attack on the U.S. Capitol.

And, most of all, the self-effacing and affable executive has been perhaps the most loyal lieutenant to the Amazon founder Jeff Bezos, joining him right out of Harvard Business School in 1997 and playing no small part as the tech mogul became one of the most powerful figures in American business.

Now, with the news that the outsized Mr. Bezos will depart as C.E.O. of Amazon in the fall in favor of Mr. Jassy, the successor will face both massive challenges and enormous opportunities as he assumes control of the e-commerce behemoth.

But first, let’s reflect on Mr. Bezos, who is perhaps, along with Elon Musk, the most visionary tech executive to come along since Apple’s Steve Jobs. And, despite the jolly guffaw that sometimes obscures his bottomless aggressiveness, Mr. Jassy has been even more obstreperous and voracious than that pair when it’s come to turning Amazon into a giant.

Mr. Bezos’s ambition was clear even when I first met him in the mid-1990s. The head of a scrappy company, he raced like a dervish between the shelves of its single warehouse, talking a big game for a small and wiry 30-year-old in pleated khakis and Oxford shirts. He engaged with the media a lot back then because he needed us on his tireless climb upward. He was always in touch, explaining some new innovation that would deliver on his promise of creating the “earth’s biggest bookstore.”

Looking back, it seems like such a quaint ambition now. Amazon has marched into every arena of commerce, building moat after moat — logistical, financial, customer service — to keep its rivals from catching up. It expanded into selling its own wares, into physical retail, entertainment and into all manner of home monitoring devices. And it has its Sauron-like eye aimed relentlessly on a whole lot more than that.

Not surprisingly, the ever-larger Amazon has started to run into even bigger roadblocks. They vary as much as its businesses do, from an invented freak show competition over the opening of a new headquarters, to its attempt to clamp down on unionization, to complaints from third-party sellers about its use of data, to its astonishing and disturbing ability to expand its power amid an economically devastating pandemic and mass suffering.

And now, Mr. Bezos is headed for the exit.

He’s not exactly fading into the mist: He will remain Amazon’s executive chairman and will no doubt remain a major force at the company in much the same way Bill Gates has after stepping down from Microsoft. But Mr. Bezos has, for a long time, seemed weary of the day to day, with an eye on all the things you become interested in when you’re one of the world’s richest people — such as space travel.

In comparison, Mr. Jassy is nothing if not earthbound, and will be even more so as he struggles to move Amazon into the next and perhaps most difficult phase of its trajectory.

In that effort, he has ample examples in Satya Nadella at Microsoft and Tim Cook at Apple. Both took over from great leaders and made their companies greater and their stocks more valuable, even if they lacked the charisma and bravado of their predecessors.

But those who have tangled with him note that Mr. Jassy hates to lose any deal in the very competitive cloud space, with one observer noting that he tries to “win at all costs.” To me, that characteristic has been table stakes for most players in his sector, which includes rivals like Oracle, Google and Microsoft, none of which are known for their manners.

Still, Mr. Jassy will have to be even more willing to play hardball, given the pressures to expand the empire that Mr. Bezos has bestowed upon him while fending off antitrust investigations and other efforts by regulators to curtail its ambitions.

Will Amazon continue to press into health care? Autonomous vehicles? Should it double down on its retail ambitions or move quickly into new markets like insurance and banking? Can it keep growing its massive work force or will it have to soften the hard-charging, manic style perfected by Mr. Bezos?

That same steel will was certainly on display in a long interview I did with Mr. Jassy in mid-2019 about AWS. I have always preferred to talk to him more than almost any other Amazon executive, because he does not shirk from a debate or retreat to stale talking points. He also was not going to give an inch when it came to tougher topics like potential bias in facial recognition.

On that hot-button issue, Mr. Jassy said clearly that it was not up to Amazon to be the moral arbiter of the world, but that he would like government to step in. “People are looking for those extra sets of protections around the federal government explaining how they want the (facial-recognition) technology to be used and [to have] real ramifications if you misuse it,” he said. “And I wish they would hurry up, because if they don’t … you’re going to have 50 different laws in 50 different states.”

When I asked him about having to spin off AWS in the wake of a potential antitrust investigation — a prospect that would scare many — he shrugged. “If we were forced to do it, I guess we would have to do it,” he said. “We don’t spend a lot of time talking about it.”

It went like that for the whole interview, with Mr. Jassy playing the true Amazon believer who could handle the pressure and plow on, polite but firm, reasonable but relentless. It made it clear to me then why he would be the one Mr. Bezos would ultimately pick as his successor.

As we were leaving the stage, I told him so and he just shrugged. “I never waste my time thinking about stuff like that,” Mr. Jassy said, laughing. “You shouldn’t either.”

No longer.

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