Fresh out of Israeli national service, a young Shai Weiss headed straight for South America. The year was 1990 and he had saved $5,000 to sate his wanderlust.
“The cheapest place I ever slept was a hotel called The Ritz in southern Chile – 75 cents a night,” he recalls. “I had no expectations – I went by price.”
So how was it? “Well, it was not The Ritz,” he admits. “But you’ve got to take risks in life – calculated risks.” Weiss knows all about risks; he’s made a career of them.
It is with a warm smile he greets me at Virgin Holidays’ plush Kensington High Street store. I arrive eager to learn more about Virgin Atlantic’s recently appointed chief executive, the man tasked with leading a new era of growth for the airline after taking the reins from Craig Kreeger in January.
Born and raised in Jerusalem to a doctor and art historian, Weiss – along with his brother and sister – enjoyed what he describes as a typical Israeli upbringing.
“I went to a good school which was very conducive to learning, especially self-learning,” he tells me. “I was fortunate, during my childhood, to live in Windsor for a year in 1975.
“We then moved to Houston, Texas, in 1976 for two years, which changed my outlook on life. I’d experienced other cultures and developed a fascination with the world beyond Israel. From an early stage, my outlook was always international.”
Aged 18, Weiss embarked on three years’ mandatory service in the Israeli Defense Forces, opting to stay on for a fourth. “Was it a good experience?” he muses. “First of all, I had no choice – the only choice I had was to do the best I could. But to have that responsibility to lead so early in life was extremely formative.”
Weiss returned to Israel following a gap year to study business, and was quickly presented with another opportunity to broaden his horizons. He moved to New York, working by day for the Israeli Ministry of Defense while studying finance by night, earning a place at Columbia Business School and, eventually, an MBA.
A career beckoned with a major financial organisation and, sure enough, Weiss landed a job with Morgan Stanley’s mergers and acquisitions group in London.
However, a call from a former client changed everything in 2001. Telecoms giant NTL was on the brink; Weiss was parachuted in as part of a turnaround team. It was undoubtedly a risk. The telecoms and media landscape was changing rapidly with the advent of home broadband and mobile phones. It would have been easy to get it wrong.
In November 2004, he pitched to Richard Branson an ambitious merger of NTL:Telewest, Virgin Mobile and Virgin.net. “It was a complicated transaction,” says Weiss. “But about two years later, it kind of worked out. And that’s where my story with Richard and Virgin started.”
Virgin Media was eventually sold in February 2013 to Liberty Global for $23 billion (£15 billion). Some turnaround from the brink of bankruptcy.
Weiss went on to establish, with Branson, the Virgin Green Fund – an investment programme focusing on renewable energy and other tech. In 2012, he joined the Virgin Atlantic board and, in a peculiar stroke of fate, interviewed the man who was to become his predecessor – Kreeger.
Weiss was appointed Virgin Atlantic’s chief financial officer in July 2014 and chief commercial officer in January 2017 before it was announced in June last year he would take the helm.
“Craig was an unbelievable CEO,” says Weiss. “When there was an opportunity to join Virgin Atlantic and work with Craig, I didn’t hesitate. I don’t view career planning as a linear process; I’m still new to aviation, but I’m a quick study.”
“Be useful” is Weiss’s mantra, citing Good to Great author Jim Collins. “If you’re useful, things happen. Did I have a vision of joining a large company? No. Did I have a vision of making a difference and leading people? Absolutely.
“I always encourage people to take calculated risks, bet on themselves and have a great sense of what they want to achieve. But be loyal.
“Everyone has to take stock of where they can make a difference… I figured I could make a difference leading people, especially through change”
“A lot of people move too quickly and don’t give themselves time to reach peak performance, which is when you absolutely recognise the patterns ahead of you, make the best decisions with imperfect information, and have a team who know you’re there for them. At peak performance, the opportunity set is much bigger.
“I think there comes a time when everyone has to take stock of where they can make a difference. I figured I could make a difference leading people, especially through change. We knew there was a lot to do to transition Virgin Atlantic into a period of growth, innovation and bold thinking.”
This period of growth has now arrived. Virgin has already this year announced new routes to Tel Aviv and Sao Paulo, while in partnership with Delta, it will add Boston Logan and New York JFK from Gatwick next summer.
The airline last week welcomed the first of its new Airbus A350s, and expects to expand its transatlantic joint venture with Delta later this year.
“What we’re seeing is the tip of the iceberg in terms of the decisions we’ve made,” says Weiss.
Perhaps the most eye-catching development is the airline’s acquisition of Flybe to provide regional feed for Virgin’s Heathrow, Manchester and Gatwick bases. Comparisons have been drawn with Virgin’s short-lived feed carrier Little Red, which Weiss embraces.
“Launching, operating and shutting Little Red does not mean the idea wasn’t right,” he says. “People ask what the difference will be with Flybe. My cheeky answer is 8.5 million passengers. Flybe is an established network, with load factors of 80% and slots at Heathrow. It’s something we contemplated with BMI, tried with Little Red, and I believe will ultimately be very successful with Flybe.
“The foundation of my work didn’t start on 1 January,” he continues. “It started with Craig’s ‘plan to win’ and now Velocity [a new corporate plan]. That is what 2020 will bring. Of course things will change, but we have a clear purpose to become the most-loved travel company.
“People always ask how I avoided friction with Craig [during the handover]. It was actually a very well coordinated transition. Anything to do with 2018, Craig was in charge; anything to do with 2019 and beyond, I would take the lead.”
More change is coming. Virgin has committed to doubling black, Asian, and minority ethnic (Bame) representation to 12% and ensuring equal gender representation across its leadership team. “These are firm targets we will measure ourselves on up to 2022,” says Weiss.
The airline recently announced its iconic “Varga Girl” figurehead would be retired and replaced with five new, more diverse “flying icons”, which Virgin says represent the changing face of the business, its staff and customers. It has also relaxed makeup rules for cabin crew.
“That move actually came from our staff,” Weiss reveals. “I love the fact they felt able to ask why we thought it was appropriate in this day and age to tell people how they should appear.”
The airline’s Heathrow-Newark Pride flight on 28 June, meanwhile, has sold out. Weiss tells me they could have sold it out 10 times over.
“Launching, operating and shutting Little Red does not mean that the idea wasn’t right”
Virgin’s pursuit of cleaner fuels continues apace too. Weiss says work to establish a UK biofuel base with partner LanzaTech is “in motion” and stresses Virgin would share any advancements with the rest of the industry. “There are great benefits to being first,” he says. “And we’d want to be rewarded for the risks we’ve taken. But whoever cracks the code should share it with everyone. The matter is so significant it can’t be viewed just as a business advantage.”
Which brings us back to Weiss’s point about calculated risk. “We are all inhibited by what we think we can or can’t do, what the market will or will not bear, and what will happen if things don’t work out,” he says. “I’m a positive person. I think, ‘what happens if things do work out?’.”
Is it working out at the moment? “Time will tell,” he says, with a knowing smile.
September 2012: joins Virgin Atlantic board; July 2014: appointed chief financial officer; January 2017: appointed chief commercial officer; January 2019: appointed chief executive.
Weiss grew up in Ethiopia Street, Jerusalem. The name stayed with him; now Weiss wants to take his family on holiday to the East African country.
Weiss on jetting off: “I like getting to know other cultures; I like mountains; I like walking. We’ve spent a lot of time in Asia – Thailand, Cambodia, Vietnam, Hong Kong. But our last trip was Cape Town over Christmas.”
Weiss lives in London with his family, watches Arsenal when he can, reads The New Yorker and “attempts” to play basketball.
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