“Who Is He?”: Andy Jassy, Amazon’s New CEO, Enters the Ring

It was just another Tuesday in Seattle when Andy Jassy sat down in his office at the Amazon re:invent building, one of many on the sprawling campus, to take what would end up being the most important phone call of his life. Seattle is often gloomy and wet during the winter months, but on this particular January day, the rain was torrential, slamming against the windows of the 37-story high-rise. In the distance, the Seattle Space Needle disappeared between the clouds as if it were threaded through the sky. Inside, the building was quiet. Jassy, who is 5 feet 10 inches tall with an oblong face and short, spiky hair, was dressed in a variation of the same outfit he always wears, a dowdy button-down with worn-out jeans and leather high-tops with a white sole.

That day, just like every day for the past two-plus decades, Jassy had been the first person into the office, arriving in his 1998 Jeep Cherokee Sport, the same vehicle he has been driving since moving to Seattle in 1997, when he took a job at Amazon the Monday after he finished business school at Harvard. Unlike most Amazonians, who worked from home as the COVID-19 pandemic ravaged the world, Jassy had been making the trek to the office from his home in the Capitol Hill neighborhood to run Amazon Web Services (AWS), the biggest cloud storage business on the planet, with more than $50 billion in annual revenue (more than double that of Salesforce).

A few hours earlier, Jassy had received an email from his boss, Jeff Bezos, the CEO of Amazon, asking if they could talk on the phone. Bezos-level requests weren’t a regular occurrence for Jassy, usually landing in his inbox every couple of weeks, so such a note meant there was something important to discuss—perhaps a problem in one of the company’s three dozen divisions, which oversee everything from top secret government contracts to the making of toilet paper. Jassy’s seventh-floor office was a panopticon of whiteboards, each one filled with endless Amazon-related to-do lists or ideas. He had so many whiteboards that his office walls were barely visible. Some of the notes on the boards were so secret that he would cover them during meetings. That day, he sat at his desk and dialed his boss. Bezos greeted Jassy with a bit of small talk—some personal, some business. Then, out of nowhere, Bezos said something Jassy never expected to hear.

“I’m contemplating stepping away from the CEO role at Amazon,” Bezos said, as recounted to me by Jassy. “I’m happy to keep doing the role, but I’ll only stop doing it if you’re excited about being the next CEO and my successor.”

“Can I think about it for a couple of days?” Jassy asked, surprised and excited by the prospect but obviously taken aback by the seemingly sudden offer.

“Of course,” Bezos replied.

Jassy is a creature of habit and tradition to an unusual degree. He meets each of his two kids, a son and a daughter, for breakfast once a week (always independently), on the same day at the same time, and has done so for years. He hosts the same weekly, monthly, and annual sports gatherings at his house. He schedules two hours for himself on his calendar once a week to read (often Amazon-related memos), and on Tuesdays, as he’s done for the past 25 years, he has a date night with his wife, Elana.

That night, seated outside at a local restaurant with plastic domes installed over each table to help separate patrons from one another, with the rain pelting down on them, the Jassys discussed the pros and cons of taking the biggest and most visible CEO job on the planet. Were he to accept, Jassy would oversee 1.4 million employees at a company with a market capitalization of more than $1.75 trillion; he would oversee the divisions that build electronics, make clothing, sell books, grow food, procure data, and dish out pharmaceuticals; not to mention continuing to oversee his brainchild, the cloud-services division, which props up most of the internet. If he chose to take this daunting job, he would be responsible for Amazon’s Alexa, Ring, and Twitch; Whole Foods Market; IMDb; ComiXology; Audible; Amazon Studios, the makers of The Boys and The Marvelous Mrs. Maisel; not to mention hundreds of fulfillment centers, a mammoth supply chain, and countless other businesses that start with Amazon: Amazon Advertising, Amazon Fresh, Amazon Drive, and on and on.

WHEN I MENTIONED TO PEOPLE I WAS WRITING ABOUT ANDY JASSY, ALMOST EVERYONE RESPONDED, “WHO IS HE?”

This job would inevitably lead him to be dragged in front of Congress, cameras glaring and angry politicians trying to tear him apart, where he would be forced to answer questions about Amazon’s monopolistic business practices and a slew of antitrust issues. He’d be ridiculed on TV, turned into a million unflattering animated GIFs on social media, and see his name and face shackled to the front pages of a thousand newspapers. It was a role that would put him on the front lines of the war with Amazon employees trying to form unions, where he would have to personally hold at bay tens of thousands of competitors and stave off foreign governments that want to break Amazon into a million little pieces. Perhaps most difficult of all, if he took this job, Jassy would somehow have to sustain the truly astounding growth trajectory of the company, which continues to show a 37 percent increase in revenue year over year and brings in $443 billion in annual revenue.