Not surprisingly, the ever-larger Amazon has started to run into even bigger roadblocks. They vary as much as its businesses do, from an invented freak show competition over the opening of a new headquarters, to its attempt to clamp down on unionization, to complaints from third-party sellers about its use of data, to its astonishing and disturbing ability to expand its power amid an economically devastating pandemic and mass suffering.
And now, Mr. Bezos is headed for the exit.
He’s not exactly fading into the mist: He will remain Amazon’s executive chairman and will no doubt remain a major force at the company in much the same way Bill Gates has after stepping down from Microsoft. But Mr. Bezos has, for a long time, seemed weary of the day to day, with an eye on all the things you become interested in when you’re one of the world’s richest people — such as space travel.
In comparison, Mr. Jassy is nothing if not earthbound, and will be even more so as he struggles to move Amazon into the next and perhaps most difficult phase of its trajectory.
In that effort, he has ample examples in Satya Nadella at Microsoft and Tim Cook at Apple. Both took over from great leaders and made their companies greater and their stocks more valuable, even if they lacked the charisma and bravado of their predecessors.
But those who have tangled with him note that Mr. Jassy hates to lose any deal in the very competitive cloud space, with one observer noting that he tries to “win at all costs.” To me, that characteristic has been table stakes for most players in his sector, which includes rivals like Oracle, Google and Microsoft, none of which are known for their manners.
Still, Mr. Jassy will have to be even more willing to play hardball, given the pressures to expand the empire that Mr. Bezos has bestowed upon him while fending off antitrust investigations and other efforts by regulators to curtail its ambitions.
Will Amazon continue to press into health care? Autonomous vehicles? Should it double down on its retail ambitions or move quickly into new markets like insurance and banking? Can it keep growing its massive work force or will it have to soften the hard-charging, manic style perfected by Mr. Bezos?