As Andy Jassy prepares to step into Jeff Bezos’ shoes as chief executive officer of Amazon, theCUBE is offering a retrospective on how Jassy has shaped the enterprise computing landscape, and we will explore the changes he could bring as Amazon’s incoming CEO.

“Andy now is becoming ‘Andy Jassy, the most important executive in the world,’” SiliconANGLE co-founder John Furrier said during a special digital CUBE Conversation on Jassy’s promotion to lead the e-commerce giant.

Jassy is no stranger to theCUBE, SiliconANGLE Media’s livestreaming media studio. TheCUBE and SiliconANGLE have been closely following his rise since 2012,  as he correctly predicted and heavily influenced nearly every turn of the cloud computing sector. Perhaps no one in the media has covered Jassy, a regular on theCUBE, more intimately.

From Furrier’s first exclusive with Jassy in January 2015 to the most recent exclusive interview series during re:Invent 2020, theCUBE has had an insider’s view of AWS as it grew to dominate the cloud computing market.

Andy Jassy talks with John Furrier and Dave Vellante during re:Invent 2018

AWS unintentionally disrupted the tech world

TheCUBE has covered AWS’ annual re:Invent conference since it started in 2012. In the event’s second year, we reported on the 235 new services and updates announced as part of Jassy’s aggressive stance toward cloud adoption. This proliferation of releases was to become a hallmark of the event, with 2014 distinguished by the launch of AWS Lambda serverless compute.

By 2015, AWS’ reputation as an industry disruptor was well established, but the company wasn’t created with the aim to change the tech world. As Jassy told theCUBE in 2015, AWS grew organically out of Amazon’s frustration with its ability to launch new projects and support customers.

Speaking for the first time with theCUBE during re:Invent 2015, Jassy described the disruption as a side-effect of Amazon’s “working backwards” customer-centric mindset. “We are not trying to be disruptive; we are trying to give the customer what they want,” Jassy said. “Everything we do is about the customer and customer experience.”

Early in 2015, Jassy spoke off-camera with Furrier and Vellante. The resulting Forbes article was Jassy’s first personal profile as leader of AWS and accurately predicted the trillion-dollar total addressable market potential for cloud computing.

“People thought we were crazy,” Furrier recalled. But theCUBE, and Andy Jassy, knew better. Amazon had established that customers wanted things faster and cheaper, and when Jassy applied that model to cloud computing “it was completely disrupted,” Furrier said. “Jassy specifically would say to me many times that ‘to eliminate the undifferentiated heavy lifting’ was a key principle of what they were doing.”

Thanks to AWS, speed, agility and simplicity have become the mantras not only of cloud computing, but of business in general. “There’s no distinction between enterprise and society, and that’s clearly because of the rise of cloud computing and the rise of Amazon Web Services,” Furrier said.

Jassy and Furrier during re:Invent 2015

In the room where it happened

Over the next five years, Jassy not only gave on-camera interviews with theCUBE during AWS’ annual re:Invent conference, but spoke with Furrier at length on the cloud computing industry and his goals and strategies. A quick check revealed the SiliconANGLE site returns hundreds of results for “Andy Jassy,” and the videos of his appearances on theCUBE have been viewed hundreds of thousands of times to date.

We were there in 2016 when Jassy and then-VMware Inc. CEO Pat Gelsinger announced the landmark partnership in which VMware users were able to move computing jobs run on VMware software to AWS’ cloud in order to take advantage of more flexible and lower-cost storage and computing services.

It was a move that “saved VMware,” according to Furrier. “Jassy does these kinds of deals. He’s not afraid. He’s got a good stomach for business, and he’s a relentless competitor.”

2016 also saw Jassy’s first profile as theCUBE’s Guest of the Week. Celebrating its 10th birthday, AWS had recently been described by Gartner as not only the main force in cloud computing but “several times the aggregate size of the next 14 cloud providers combined.” In the interview, Jassy discussed how he adheres to Amazon’s Leadership Principles in every decision he makes.

“I think they have been the single most important reason we have been able to scale as fast as we have and scale across the world the way we have, without losing our culture,” he said.

Holding the lead

Holding onto that lead became the topic of conversation when Jassy sat down with Furrier for a two-hour interview in a Seattle restaurant. It was 2017; enterprises were starting to adopt cloud and AWS was the 800-pound gorilla in the room. Established enterprise vendors such as Oracle Corp. and Microsoft Inc. had underestimated AWS’ abilities, but Jassy was confident of the direction cloud would progress.

“It’s kind of wacky these days to build a data center,” he said in the first of an exclusive three-part interview series with Furrier. “While I still characterize it as the early days of adoption, make no mistake: Enterprises are not just dabbling in the cloud. They are using AWS and the cloud in a very pervasive way.”

By 2018, AWS was starting to rival Amazon’s e-commerce division for the variety of products it offered. Re:Invent brought a slew of releases aimed at edge computing, the internet of things and machine learning. Outposts saw the company provide on-premises data center systems architected, like the AWS public cloud, enabling a subtle move toward hybrid cloud. There was also the launch of AWS Ground Station, which rocketed the internet into outer space.

“There’s this real, palpable excitement about these new workloads and these new capabilities,” Jassy told Furrier in yet another lengthy exclusive interview — this time held in Jassy’s own basement sports bar he calls “Helmet Head.”

Andy Jassy and John Furrier at Jassy’s basement sports bar he calls “Helmet Head.”

“He’s not afraid to take chances on the product side,” Furrier said. “He’ll go in and take a chance on a new market.” He sees this as a good trait for Jassy as he faces possible government regulations targeting the dominance of tech giants such as Amazon. “I think he’s going to have to apply that pragmatic experimentation to new business models,” Furrier recently said of Jassy.

The rapid pace and variety of AWS innovation caused some to question the company’s approach as “scattershot.” But once again the strategy was born from Amazon’s e-commerce roots and the desire to give customers what they want and need.

“For the first seven or eight years of Amazon, we basically jumbled together parts of our technology, and we were moving really quickly,” Jassy told theCUBE in an interview during re:Invent 2019. “It was this big ball, this big monolithic piece. We got religion about that in having to move faster in the consumer business and tease those pieces apart.”

2020 keynote hints at Jassy’s future

Unlike many chief executives, Jassy intimately knows the technology behind the products and he’s not afraid to talk details. In fact, the CEO is known for his lengthy keynotes. During the virtual re:Invent 2020, Jassy spent his keynote underscoring the event’s message of “Amazon Everywhere” and warned companies to adopt cloud fast or risk the consequences.

“You have got to realize that if something’s going to happen, it is going to happen regardless of whether you want it to or not,” Jassy said. “You’re much better off cannibalizing yourself than having someone do it to you and chasing it.”

Jassy probably knew he was slated to become Bezos’ replacement when he took the stage for that keynote. But did he hint at his strategy for the future of Amazon? The first of eight steps he gave for reinvention in the post-COVID digital age was “Leadership has to have the will to invest and reinvent.” That matches with Amazon’s leadership principle to “Invent and Simplify,” which states that leaders are “are externally aware, look for new ideas from everywhere, and are not limited by ‘not invented here.’”

Furrier with Jassy during re:Invent 2016

Broader than cloud

Jassy “likes to build stuff” Furrier pointed out, comparing the understated AWS CEO to Elon Musk in terms of mindset. While Jassy’s technical expertise is well-known, he is also a fan of music, sports and media, according to Furrier, who predicts Amazon’s convergence of media, technology and art will continue under Jassy’s command.

“Having a new leader like Andy Jassy will enable next-generation talent,” Furrier predicted. “It’s going to be very interesting to see.” So while Jassy himself may like to keep a low profile, Amazon will continue to innovate and hit the headlines under his guidance. “He just wants to do what he does, and he lets his game do the talking,” Furrier added.

Perhaps the best indicator of how Jassy will lead Amazon comes from his statement on how he built AWS, told to Furrier during an extended on-camera interview as part of a full series of one-on-ones during theCUBE’s coverage of re:Invent 2020.

“We were trying to build a business that outlasts all of us and that is successful over a long period of time,” Jassy said. “The best way I know to do that is to listen to what customers are trying to solve and invent on their behalf, even if it means in the short term you may cannibalize yourself.”

Here’s Furrier and Vellante’s complete analysis of what’s next for Amazon under Jassy:

Photos: SiliconANGLE