All those connections make Brian Neider, Lead Edge Capital Partner, "super comfortable" and "pumped" with the choice, he told CNBC's "Squawk Box" on Monday, adding that it would be great for Uber to get the stamp of approval from funds like SoftBank.
While Kalanick has come under scrutiny for his lack of soft skills, Khosrowshahi has spent years honing them, according to a deeply reported profile in the Puget Sound Business Journal last year.
"This is a guy who could spend a decade working side-by-side, very successfully, with [IAC's] Barry Diller, who is no shrinking violet," Jeff Sonnenfeld, senior associate dean for leadership studies at Yale, told CNBC's "Squawk on the Street" on Monday. "I think that speaks legions for him."
And that's helped him restructure Expedia many times over, making deal after deal. That's something something Uber's been trying to do, selling off its Russian and Chinese businesses into new joint ventures and examining options for its leasing division.
Khosrowshahi was the head of corporate development, mergers and acquisitions for the companies that became media conglomerate IAC.
"When Expedia was struggling, he went in and became the lead operating executive. He uniquely possesses both operating capabilities as well as capital markets capabilities, which not a lot of global executives have. It's a nuance that Wall Street appreciates, but it's hard to understand," Gerstner said. "That's really pertinent to a company like Uber that's strategically competing on a global basis. They have to figure out how to compete in all those different markets -- and to partner, sell, or operate on a stand-alone basis."
Plus, Uber has a slew of vacancies to fill: President Jeff Jones left the company. The search for a chief operating officer is still underway, and the executives in charge of business, finance, communications, engineering and self-driving cars are all out the door.
"He knows how to identify talent," Gerstner told CNBC. "He knows what a world-class executive looks like. He has the frame of reference to evaluate candidates who exist within Uber and also has the network to attract the talent needed to take the business to next level."
Then there's hard-charging former CEO Travis Kalanick, who is still on the board of the company and poses "personality" issues, one investor said.
"It seems to me, from what I've read and what I've seen from other people covering this, that Dara is the type of person that's going to come in and institute a culture that's going to take away some of those distractions and probably put them on a more professional business path," Paul Holland, an Uber investor and general partner at Foundation Capital, told CNBC's "Squawk Alley" on Monday.
"And I think to that extent, as a major shareholder, whether it's Travis or anybody else, they should all be pretty excited about this. And I suspect folks will get behind him to drive the company, ultimately towards an IPO."
— With reporting by CNBC's Deirdre Bosa