Andy Jassy Is Rewriting Amazon's Playbook for the AI Age

May 14, 2026 at 5:00 PM EDT

Listen: How Andy Jassy Is Steering Amazon Through the AI Boom Without Bezos

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Thirteen miles north of Jackson, Mississippi, past the self-storage facilities, a Nissan factory and a Coca-Cola bottling plant, five enormous rectangular buildings rise from the state’s mineral-rich red clay. A few years ago, this was rolling pine forest, earmarked for development by the local planning authority. Now it’s part of a $25 billion cluster of state-of-the-art data centers. The company behind this mammoth undertaking once popularized the act of buying stuff online and later the corporate custom of running computer applications in the cloud: Amazon.com Inc.

On a tour of the site in March, Rich LeBron, a former US Navy captain who now runs Amazon’s campaign to stand up a fleet of data centers in the state, gestures past the wire fence that cordons off a bustling construction zone. “That wasn’t there last week,” he chuckles, pointing at one of a dozen new steel structures planned for the site, each of which costs roughly $1 billion. Inside one of them, on the other side of steel fire doors that remind employees to leave behind their cellphones and smartwatches, is the reason for that massive expense. There are hundreds of black cabinets, each more than 7 feet high, filled with pizza-box-size trays of AI accelerators, memory chips and batteries, all connected by color-coded power and networking cables and cooled by industrial fans that expel the heat generated by quintillions of math calculations each hour. The data center was constructed for Anthropic PBC, maker of Claude, the popular chatbot.

About 3,000 construction workers toil here, and they’re generally in awe of the project. They’re a bit fuzzier on the exact name of the guy who commissioned and financed it, though. On the tour, a guide refers to him as Andy Jazzy.

This July will mark five years since Andy Jassy took over the chief executive officer role from Amazon’s founder. At the corporate offices in Seattle, the workforce has grown accustomed to his brand of rigorous oversight and ongoing exhortations to act as if they were at Jeff Bezos’ startup, not a $2.9 trillion behemoth. He recently placed a series of staggeringly expensive bets on artificial intelligence, audacious even by the standards of Silicon Valley’s ongoing trillion-dollar AI bacchanalia. In February he agreed to invest as much as $50 billion in OpenAI in a deal that commits the rising startup to relying in part on Amazon’s data centers and custom-designed microchips. Then in April he expanded a similar partnership with its archrival, Anthropic—a $13 billion investment, with an option for an additional $20 billion. To Jassy’s critics, that spending was the price of Amazon’s late jump into the current AI wave. He wasn’t bluffing, though: Jassy spooked investors by vowing to spend $200 billion this year on big-ticket items including warehouse robots, a far-out effort to launch satellites into space, and in particular more AI data centers, AI chips and networking equipment. “I don’t think the world has ever seen a technology get this much adoption and grow this quickly, at least in my lifetime,” Jassy tells Bloomberg Businessweek.

“You can choose to howl at the wind, but AI is not going away”

Jassy runs the fifth-largest company in the world by market value. He takes pains, earnestly and often awkwardly, to project an everyman image, in part by constantly advertising his lifelong passion for music and sports. In the anteroom to the executive suite in Amazon’s “Day One” headquarters on a rainy morning in April, the Who’s Tommy plays on a turntable. On the wall is a display of album covers (Ramones, Pink Floyd) and baseball caps (Seattle Kraken, New York Giants).

He also studiously strives to embody one of Amazon’s 16 leadership principles, frugality, as if to compensate for Bezos’ public evolution into an icon of overindulgence. Jassy drives himself to work in a ’98 Jeep Cherokee, even though he imagines the airbags might “pulverize” him if they ever deployed. His favorite beer is Manny’s, a Seattle microbrew and fixture at the city’s sports bars and dives. To his Businessweek photo shoot, he wears what he calls his “eight-minute blazer,” which he once bought in a hurry for a customer meeting. “He’s customer obsessed, product obsessed and, frankly, Amazon obsessed,” says his Harvard classmate Gina Raimondo, the former US secretary of Commerce. “It’s really the only place he’s ever worked.”

Featured in Bloomberg Businessweek, June 2026. Subscribe now. Photographer: Holly Andres for Bloomberg Businessweek; Illustration: Petra Pétterfy

The company is much different from the online bookseller Jassy joined in 1997. Amazon today is a corporate turducken: an advertising business and logistics company stuffed inside an e-commerce marketplace, trussed to a cloud computing powerhouse, and garnished with Alexa, Whole Foods Market and Prime Video. The behemoth infuriates critics, who lambaste its rough treatment of drivers and warehouse workers and its willingness to bully rivals. On the other hand, ordering from Amazon and seeing a cardboard box sitting on your doorstep the next day is one of the few reliable luxuries of modern life, made possible only because of the company’s ruthless ability to root out inefficiencies, adopt cutting-edge robotics and hide all the messiness from our delicate eyes.

Jassy took over in mid-2021 and had to correct course from some of the excesses of the late-Bezos era, including a spurt of overhiring to meet pandemic demand. He laid off roughly 60,000 corporate personnel, forced employees back to the office and shuttered dozens of projects, such as the cashierless Go stores, Amazon Fresh supermarkets and a telehealth service. Employees grumbled, but his personal style contrasted favorably with his former boss’s. He was ever-present, probing but never argumentative. (Jassy for years has urged colleagues to not be afraid to ask dumb questions.) He also has the agreeable habit of thanking everyone at the beginning and end of meetings and sending holiday cards to his senior execs. Friends vow that it’s all authentic and not at all humility theater for a leery public that’s become profoundly skeptical of technology overlords.

Amazon’s Jassy Era

Sources: Bloomberg, company reports

Then came the age of generative AI, inaugurated by OpenAI’s ChatGPT in late 2022, which posed perhaps the first existential challenge to Jassy’s own baby and Amazon’s profit engine, Amazon Web Services. With AWS, Amazon invented cloud computing and went on to build a client list that included the biggest names in corporate America. It remains the market leader, though Microsoft Corp. and Alphabet Inc. have collectively booked $600 billion more in future business than Amazon since ChatGPT came on the scene. Would companies and governments move their data off Amazon’s servers to access the newest large language models? Would shoppers, for that matter, start browsing and buying with knowledgeable chatbots such as ChatGPT and Google’s Gemini, instead of enduring the ad-riddled search results on Amazon.com?

The answers to those questions, and how Jassy navigates the AI era, will matter more than anything else in determining whether Amazon continues to thrive in its fourth decade and how posterity comes to view Bezos’ successor. Some of Jassy’s moves have seemed contrarian. While the world swooned over ChatGPT, Amazon executives told anyone who would listen that the market would be bigger than any one chatbot. Jassy cozied up to Anthropic, getting Amazon corporate customers access to Claude and buying time for Amazon to develop its own alternative. He decided that Amazon should be, of all the crazy things, the Amazon of AI, then assured investors, employees and the public that resisting the coming changes wrought by AI would be futile. “I can understand how, when there’s the potential for this much change, it can make some people nervous. I just happen to think it’s going to make so many things better,” he says. “You can choose to howl at the wind, but AI is not going away.”

Jassy (No. 13) with his high school soccer team.

Jassy never intended to spend his life in the Pacific Northwest. He grew up outside New York City, in a well-off household with doting parents. During business school, he agreed with his Los Angeles-raised girlfriend and now wife, Elana (via contract, scribbled on a bar napkin, of course), to spend a few years out West before returning to New York. Jassy applied for jobs over the summer and enjoys telling the story of how he ended up interviewing at Walt Disney Co. Asked to name an incredibly successful product, without picking Nike or other obvious choices, Jassy blurted out Beavis and Butt-Head, touting the cartoon’s creative merchandising.

Jassy didn’t get the job—telling the story is perhaps more humility theater. But to fulfill the contract with Elana, he worked for a digital stock photography company one summer in Seattle and loved the city. Approaching graduation, he applied to a few other West Coast companies until an online bookseller, flying high in the first dot-com boom, plucked his résumé out of a stack.

Amazon was all-hands-on-deck, with employees spending weeks over the holidays in warehouses, packaging books for customers. Colleagues remember Jassy running Amazon’s first eight-person marketing team and then its fledgling CD-selling business, parroting Bezos maxims and wearing his dress shirts rolled up at the sleeves above the elbows.

Working for Bezos back then was tough. “Why should I listen to anything else you have to say the rest of this time?” he once asked Jassy in a packed meeting, after identifying some incorrect numbers in a slide presentation. Jassy persevered and impressed the boss, who selected him as his first technical adviser, or shadow, a job that consisted of trailing the CEO to meetings and then huddling with him each week to consider various opportunities. During that time, Bezos and Jassy conceived Amazon Web Services, partly to relieve IT bottlenecks at the company by building heavily automated, self-service computing tools, and in 2006 Jassy split off to run it.

One can see why, 15 years later, Bezos came to view Jassy as his natural successor. AWS attracted waves of startups like Airbnb, Reddit and Dropbox, then larger enterprises such as Netflix, Intuit and the US government, including the CIA. In 2015, Jassy and James Hamilton, a top technical exec at the company, spearheaded the acquisition of Annapurna Labs to kick-start the process of supplanting the pricey hardware in its data centers made by Intel Corp. and other companies. By 2016, AWS was generating $12 billion in sales a year. “Jeff was pretty hands-off,” says Peter DeSantis, a Jassy deputy who now runs Amazon’s AI, chips and quantum computing group. “He audited us, he poked on us, [but] that relationship has been fairly consistent over time.”

Several Amazon board members say Jassy was the clear choice even before Bezos decided he wanted to spend more time with his boat (and other endeavors like his space company, Blue Origin LLC). “It was always obvious that Andy was the right person,” says Wendell Weeks, CEO of Corning Inc. and a board member since 2016. “You could not have a higher regard than Jeff has of Andy’s builder skills, and that is the Good Housekeeping Seal of approval.”

Jassy claims improbably that he had never thought about getting promoted and says that he took a few days to consider it. “I think there was a low chance he was going to say ‘no,’ ” says Beth Galetti, Amazon’s human resources chief. “But I also think that he was taking the time to make sure that when he said yes, he was ready to go do all the things that then meant.” The week Jassy officially became CEO in July 2021, at the Allen & Co. mogul fest in Sun Valley, Idaho, Bezos worked the room

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