Shaun Stewart is the highest ranking Australian at Airbnb, heading up global vacation rentals for the $US25 billion San Francisco based company.
In the past year the 36-year-old has built a team of 30 who are working on how to make people feel like they “belong anywhere”. His team looks after destinations outside major cities or urban centres like Sydney, Melbourne, New York and Paris.
In Australia, those destinations include Byron Bay, the Gold Coast, Phillip Island, Sunshine Coast, Jervis Bay and the snow fields.
One thing he’s working on is making informal group travel, like a bunch of friends going away together, easier. His team has figured out the person who is organising the trip is often the most miserable. They’re the one paying security deposits, buying groceries, hiring cars and generally rallying the troops.
He describes it as the “second generation” of Airbnb and wants to incorporate tools which make organising group travel simpler. This could potentially include capability to split travel payments or even the cost of groceries.
“In this day-and-age none of us should be sending deposit cheques to strangers and paying for groceries in advance, hoping to recoup money from each other. There’s a way to do this, there’s different platforms to help do that,” he said.
“It’s an experience which hasn’t modernised as much as it can and we can’t wait to help develop that and differentiate ourselves to deliver that experience.”
He said at this point it’s a high-level strategy and he wasn’t sure if it was one which the company would build out internally or acquire companies which already offer these types of services and integrate them.
“It’s not about offering more homes, it’s about radically changing how we travel,” he said.
“There’s a huge area for us to get more helpful and involved in how you plan and actually travel through Airbnb, versus just the accommodation side of it.”
Market research is an important element for Stewart’s team. He often gives his team members $2,000 to spend on a competitor’s website and has the people come back and present on the experience. Stewart ends up with files of presentations with things that are wrong with travel which he says helps the company solve common issues, especially around user experience.
While Stewart has spent a big chunk of his professional career in the US, he still misses some of the small things from home, like generous annual leave policies and Australian chocolate.
He still finds himself sometimes putting on an American accent so people understand him. He also fights the time zone, as a big part of his role is building out the Australian and New Zealand markets. Taking calls in the middle of the night is normal.
But now being based in San Francisco, flying home is now much easier compared to living in London or on the East Coast of the US.
Stewart told Business Insider he had a pretty standard Australian childhood, growing up in Melbourne. He’s a middle child who played footy “pretty bad” so when he left school at 17 he wanted to do hospitality.
Learning how to do business in the US
“I thought I was at the cutting edge, until I got here,” he said about working at Airbnb.
In his late teens, Stewart moved to Sydney and enrolled at the international hospitality school in Manly, then did his work experience as a night porter at the Hilton in Melbourne.
Transferring to Switzerland, he finished his hospitality degree at the prestigious Institut Hotelier Cesar Ritz and landed a job at the Grand Hotel at the Matterhorn above Zurich.
“It was the kind of place I had to wear a tux to be a waiter,” he said.
His plan was to do international development and build hotels around the world. But then the 9/11 attacks in September 2001 struck and the tourism sector contracted.
It was at this point Stewart interviewed with a company called Travelscape, which today is Expedia. When he joined, the company was doing $700 million in transactions a quarter. Nine years later it was doing $6.5 billion a quarter.
When he left TripAdvisor he would review proposals for VCs because you’d “get a free lunch sometimes”.
It wasn’t until Stewart was teaching a night class in New York when his students kept bringing up Airbnb, but he was a hotel guy and kept trying to bring the conversation back to the topic of traditional travel which in his eyes at the time was staying in a hotel, not someone else’s home.
While sailing around Croatia a recruiter from Airbnb got in contact and convinced Stewart to join the tech company in August last year.
“My DNA is (now) online travel so there’s been nothing that’s been more disruptive then Airbnb,” he said.
Now read: The Aussie entrepreneur’s guide to San Francisco.