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How new Amazon CEO Andy Jassy built an enterprise tech juggernaut

Using lessons honed from a stint as outgoing CEO Jeff Bezos' right hand, Jassy changed the way enterprise tech is bought and sold in building the most profitable division of the company.

How new Amazon CEO Andy Jassy built an enterprise tech juggernaut

AWS CEO Andy Jassy will replace Jeff Bezos later this year.

Photo: F. Carter Smith/Bloomberg via Getty Images

Twenty-four years after he joined a small online bookseller, and 15 years after he launched a small group at that company that would become the most disruptive enterprise tech company of a generation, Andy Jassy is taking over one of the biggest companies in the world.

The CEO of AWS will become the second CEO in Amazon history later this year, following the departure of founder Jeff Bezos, Amazon announced Tuesday. Jassy is a self-taught technologist who built AWS into an enterprise tech giant, turning the technology infrastructure needed to underpin its retail operation into the most profitable division of the company.

Jassy started at Amazon in 1997 in the marketing department and was tapped as Bezos' chief of staff in 2003, learning how Bezos built Amazon's culture and operational discipline before hatching the plan for AWS. Starting with simple computing and storage services delivered remotely over the internet, AWS has gone on to define a new era of enterprise computing as well as new business models for aspiring tech companies built on or around AWS.

Inside AWS, Jassy has a reputation for sweating the details, driving the company to focus on executing its plan to deliver the most comprehensive suite of cloud infrastructure services on the planet: "The Everything Store," just for CIOs. In the early days of cloud computing, this was an uphill battle, trying to convince risk-averse business leaders to bet on an emerging technology when all they really wanted was tech that wouldn't break.

So for years, AWS focused on building features that got the folks working for those CIOs — software developers and operations engineers — excited about its potential. Rather than try to force the cloud from the top down into organizations, Jassy encouraged AWS to build services for the people who were actually doing the work, who would build their own applications and services around AWS, and come back for more.

"Lots of companies and teams can fill whiteboards full of ideas and possibilities, but at the end of the day, where the rubber meets the road is being able to execute on those ideas in a way that customers care about and that resonates, and then continue to evolve that offering," Jassy told CRN in 2015, long after AWS had established itself as the leader in cloud infrastructure computing.

In the last several years, cloud competition has become much more intense. Microsoft's decision to elevate its own cloud expert, Satya Nadella, to the CEO position in 2014 set the stage for its remarkable turnaround. Google Cloud, which reported a 46% jump in revenue Tuesday, also signaled its intent to compete head-on with AWS by naming former Oracle executive Thomas Kurian its CEO two years ago.

Those developments have forced Jassy to adjust. AWS famously started off life as a "pay-as-you-go" service, where the running joke was that the early days of the company were financed by the credit cards of Silicon Valley venture capitalists scaling their startups' computing resources. Now, at Jassy's direction, the company looks to sign customers to longer-term deals in exchange for pricing concessions, giving AWS a more predictable revenue stream and its customers an incentive to build around AWS for the long term, which makes it harder to leave its cloud down the road.

"It is really hard to build a business that lasts successfully for many years, and to do it, you're going to have to reinvent yourself. And often you're going to have to reinvent yourself multiple times over," Jassy said in December during his AWS re:Invent keynote.

One consistent source of friction between Jassy and AWS employees has been his seemingly random use of non-compete agreements — which are legal in Amazon's home state of Washington — to penalize employees and executives who have left AWS to seek opportunities elsewhere. Some executives have been allowed to leave quietly for positions at other enterprise tech companies, while others — such as Google Cloud Vice President of Marketing Brian Hall and Smartsheet Chief Product Officer Gene Farrell — were hit with lawsuits delaying their transition to their new jobs.

"He's a win-at-all-costs type of person," said Zoltan Szabadi, who now works at Google Cloud after he was sued by AWS in 2017. "This is just one of the many tactics that he thinks will help his business."

That win-at-all-costs philosophy can be linked to Jassy's love of football, and especially his New York Giants. Jassy also recently became a part-owner of the Seattle Kraken, an expansion franchise in the National Hockey League that is due to start play next year at Climate Pledge Arena — sponsored by Amazon.

Jassy finished the opening section of his most recent re:Invent keynote — a meticulously planned, marathon three-hour affair — by talking about leadership. He was talking about how companies need strong leadership to commit to investing in cloud computing, but the message was certainly broader.

"… The leadership team has to build aggressive top-down goals, to force the organization to move faster than organically it otherwise would," he said. "Setting an aggressive top-down goal forces the organization to understand that they are not going to be able to dip their toe in the water for a number of years; that you mean business. And you're going to make this change, and [set] up the right mechanisms to inspect whether you're getting the right progress."

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Gig workers protest in front of an Amazon facility in 2020.

Photo: Michael Nagle/Bloomberg via Getty Images

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