Rest assured that Barry Diller’s phone is busy and his email inbox is probably a logjam.

That’s because, according to several sources, multiple people have volunteered their names as the successor to Mark Okerstrom as CEO of Expedia Group. Expedia investors are said to be actively involved in offering advice to largest shareholder and chairman Diller given the company’s reorganization woes, and lackluster performance in 2019.

In a stunner December 4, the Expedia board triggered the resignations of Okerstrom, who’d been in the post since late-August 2017, and CFO Alan Pickerill, who had been promoted at the same time.

Skift contacted several sources with some knowledge of the search, and multiple others to handicap the succession race.

If Diller follows his past practice and taps a new Expedia CEO who has Expedia/IAC Travel/Microsoft ties, then two names prominently mentioned that would fit that scenario include Zillow Group co-founder and former CEO Spencer Rascoff, and former Orbitz Worldwide CEO Barney Harford.

Both have roots in the so-called Expedia tree.

Rascoff co-founded Hotwire when 24 years old in 1999, and sold the Priceline Name-Your-Own Price rival to Diller’s Expedia/IAC four years later for $685 million. Hotwire remains an Expedia Group brand, although it has struggled in recent years.

Harford spent more than seven years at Expedia, starting in 1999, in roles ranging from director of investor relations to president of Expedia Asia-Pacific.

Here’s our handicapping of various potential hires who have Expedia/IAC Travel/Microsoft ties, or travel industry experience outside of the Diller orbit. None of them would comment or could be reached for comment.

Spencer Rascoff

Spencer Rascoff left his post as Zillow Group CEO earlier this year as Expedia founder and former CEO Rich Barton reoccupied his prior Zillow Group CEO role at the online real estate outfit. Barton retook the reins to execute a business model shift. Rascoff remains on the Zillow board, which is stocked with Expedia, TripAdvisor, Liberty Media, Microsoft, and HotelTonight veterans, including Barton, Eric Blachford, Amy Bohutinsky, Lloyd Frink, Jay Hoag, and Gregory Maffei.

One source described Rascoff as charismatic, adding that he capably headed for several years Zillow Group, a complex public company with multiple brands. Zillow Group, from that perspective, has some parallels to Expedia Group’s brand panoply.  Rascoff served as Expedia’s vice president of lodging from 2003 to 2005, was a TripAdvisor board member for six years, and has made angel investments in travel, including for Vamo, Turnkey Vacation Rentals, Vacatia, and Room77.

Like Expedia Group, Zillow Group is headquartered in Seattle. Rascoff commuted to Zillow from his home base of Los Angeles for the last four years.

Barney Harford

Harford is close to current Uber and former Expedia CEO Dara Khosrowshahi, who remains on the Expedia Group board. Harford and Khosrowshahi earned mutual respect when their companies battled each other while their CEO tenures overlapped from 2009 to 2015. In the end, Harford more than tripled a once-struggling Orbitz’s share price to $12 before selling the business to Expedia for $1.6 billion in 2015.

Soon after Khorowshahi took the steering wheel at Uber in late Summer 2017, he tapped former rival Harford to first be his senior advisor, and shortly thereafter as Uber chief operating officer. Harford left Uber in June with Khosrowshahi saying he wanted to take a more active role in the company’s core businesses.

One potential drawback in a Harford hire is that he was accused at Uber of making insensitive racial and gender-oriented remarks, and some women executives reportedly took umbrage at his management style. He apologized for his comments, and remained as COO for another year. In the third quarter, three months after Harford left, Uber beat analysts’ expectations on revenue and profits while still posting more than $1 billion in net losses.

Darren Huston

Darren Huston, who was the president and CEO of Booking Holdings for a year and a half starting in January 2014, but was at the time was called the Priceline Group. Huston also served as the CEO of the company’s largest and most important brand, Booking.com, from September 2011 until his departure under adverse circumstances in April 2016. Huston is another figure who’s frequently mentioned as a potential Expedia Group CEO candidate.

A former CEO of Microsoft Japan and a corporate vice president in charge of the company’s consumer online businesses, Huston is currently founder and CEO of BlackPines Capital Partners. He widely gets high marks for his stewardship of the Priceline Group, but left under a cloud for a personal relationship with an employee that may hurt in the Me Too era.

Gillian Tans

Gillian Tans, an early employee of the company that became the online accommodations behemoth Booking.com, which overtook Expedia and never looked back, served as the brand’s chief operating officer for more than 13 years, and was Booking.com CEO for more than three years. Tans was forced out of that position in June under circumstances that haven’t been clearly explained as Booking Holdings CEO Glenn Fogel took on her responsibilities.

Tans currently serves as Booking Holdings chairwoman, and is slated to leave near the anniversary of her departure as CEO of Booking.com.

Tans hasn’t been CEO of a public company, but led the biggest and most important brand in online accommodations. One source speculated that Tans may be “pissed off” enough at her current employer to seek to make the leap to its rival, assuming, somewhat dubiously, that noncompete clauses can be negotiated away.

Sam Shank

Sam Shank, the co-founder and CEO of HotelTonight and currently Airbnb’s head of hotels and serviced apartments, would be “a bold choice,” as Expedia Group CEO, according to one source. Shank doesn’t have experience leading a public company, and HotelTonight is a much smaller company than Expedia Group.

On the other hand, Shank was vice president of business development for metasearcher SideStep, which was sold to Kayak for nearly $200 million in 2007, and founded and led TravelPost. SideStep acquired TravelPost in 2006. Shank has been an active angel investor in travel.

Christa Quarles

Christa Quarles served as interim and then CEO of dining reservations platform OpenTable for more than three and a half years, but left after Kayak co-founder and CEO Steve Hafner took over her duties in 2018. Quarles has has no experience running a public company, and OpenTable arguably hasn’t distinguished itself in the digital and international arenas.

Dermot Halpin

Dermot Halpin, an eight-year TripAdvisor veteran who currently is president of its experiences and rentals businesses, would be a long shot given his TripAdvisor ties, and lack of public company CEO experience. Halpin, formerly president of Expedia’s Europe, Middle East and Africa division from 2001 to 2008, gets high praise from sources. He also served on the board China’s eLong, which had been controlled by Expedia but was sold to Ctrip in 2015 after piling up losses.

Nope, Not These Folks

Other names frequently floated as possible Expedia Group CEO candidates include Uber CEO and former Expedia Group CEO, and current Expedia board member Dara Khosrowshahi; Expedia founder and former CEO, and Zillow Group CEO Rich Barton; Hotwire co-founder and TPG senior partner Karl Peterson; and GoDaddy CEO Aman Bhutani.

All are deemed to be very busy and preoccupied with their public company leadership roles, and day jobs. It would be admitting defeat, for example, if Khosrowshahi re-upped with Expedia Group as CEO. Barton is very busy remaking Zillow Group. One source said Peterson makes a ton of money, and doesn’t need to be hassled with running a public company like Expedia, as attractive as that might be to some.

Aman Bhutani was president of brand Expedia Group for more than four years until he left in August, and took the helm at GoDaddy. Highly regarded, Bhutani would have been a viable internal candidate for the Expedia Group top slot if he was still with the company. Bhutani had been passed over for the position when Okerstrom got it in 2017, and left for GoDaddy this summer.

Other names touted in conversations with industry veterans and sources close to the search include Kayak co-founder and CEO Steve Hafner, who also leads OpenTable; HomeAway co-founder and CEO Brian Sharples; former SideStep CEO and current GoFundMe CEO Rob Solomon, and Technology Crossover Ventures partner Erik Blachford, who was formerly CEO of IAC Travel/Expedia.

Hafner would have a tough time exiting from rival Booking Holdings and wouldn’t necessarily be a cultural fit at Expedia. Sharples never stood out as a digital maven at HomeAway, and in fact looked to Expedia for help in the vacation rental company’s transition from a subscription business model to online booking. Solomon didn’t distinguish himself as president and CEO of Groupon from 2010 to 2012. And Blachford, with wide travel industry and investor experience, didn’t survive in his role under the Diller umbrella when he was president of IAC Travel/Expedia from 2003 to 2004.

Several travel industry wags keep touting Hafner as their bet for Expedia Group’s next CEO. “Hafner would be the single best choice,” said one after this story was published. “He’s a true entrepreneur and a great leader. Maybe smarter than Barney. I’d love to work for him. But he’s a ball buster. Which I think Expedia needs. The lack of vision within Expedia is demoralizing and Hafner could fix that.” Hafner is believe to have a non-competition agreement, however, with his employer, Booking Holdings.
Different Direction

While Rascoff and Harford could be leading candidates for the Expedia Group CEO post, Diller and the Expedia board, which will be actively involved in the selection, could go in a totally different direction. While potential internal Expedia candidates,including executives such as John Kim, president platform and marketplaces, and Cyril Ranque, president travel partners group, don’t appear to be in the serious running for the CEO position, Diller and the board could go outside the Expedia tree and choose someone with little or no travel industry experience. Perhaps someone from Amazon or Google could be in the consideration set.

There is a possibility, though, that Diller could tap Peter Kern, vice chairman of the Expedia board and the individual that Diller picked to “jointly preside,” along with Diller, over the company’s daily operations, to take on the CEO role. Kern, who’s been on the Expedia board since IAC spun off Expedia in 2005, obviously has Diller’s confidence.

Kern, managing partner of InterMedia Partners VII, however, is short on online travel operational experience. Is now the time to gamble on a board veteran with such a resume?

But with Diller pledging to “accelerate growth in 2020” — he didn’t specify top or bottom line growth, or both — it doesn’t appear highly likely that he and the board would want to take the chance of bringing on a top executive who would have to navigate a travel industry learning curve.

Diller and the Expedia board’s ultimate selections will be crucial for the evolution of the company given the dynamic technology and highly competitive market environment, and the fact that it is rare to have to replace two key executives — a CEO and CFO — potentially simultaneously.

Although it would be unfair to pin Expedia’s woes solely on Okerstrom and Pickerill, it’s clear that Diller blundered at the time of the Okerstrom appointment in 2017 when Diller said there really never was no other serious candidate under consideration to replace then-CEO Dara Khosrowshahi, who left to head up Uber. So Diller and the Expedia board need to get this set of picks right — and probably this should happen sooner rather than later.

Note: Stay tuned for a followup article on Expedia’s path forward.

Updates: This story has been updated to reflect the possibility that the Expedia Group board could potentially decide to elevate its vice chairman, Peter Kern, to the CEO position. This story has also been updated to reflect sentiment that Kayak and OpenTable CEO Steve Hafner would be a sage choice, according to some, as the next Expedia Group CEO.

Photo Credit: Expedia Group senior executive Barry Diller is searching for a CEO to replace Mark Okerstrom. Diller is shown November 14, 2019 at the company's partner conference in Las Vegas. Adam Shane Productions / Expedia Group