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

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.

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.  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. “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.”

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.

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.

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