Leslie Cafferty travels a lot. Given that she’s the chief communications officer of travel tech group Booking Holdings, that shouldn‘t come as a surprise, but even the keenest jet-setter might find her schedule alarmingly hectic.
When we speak on a Thursday, she’s in France for an advertising conference. At the weekend, she’ll be back with her family in the US. On Monday, she’ll be heading back across the Atlantic to Amsterdam for a team meeting at the HQ of Booking.com, the group’s flagship brand. It’s not an uncommon itinerary, as she balances spending time with colleagues in Europe and the US, where Booking Holdings is based.
“I know how to get myself to sleep quickly on the red-eye,” Cafferty says. “I’m on the road half the time. When I’m not, I’m working across different time zones. I start meetings by 6am, so that I’m done by 4pm when I am at home. That wouldn’t work for everyone, but it does for me.”
She has been leading Booking Holdings’ comms team for more than 10 years. It’s a varied role at a group that also features brands such as Kayak, OpenTable and Rentalcars.com. Cafferty sits within the parent company, in charge of the communications strategy for a concern that collectively employs more than 20,000 people worldwide.
The job suits an assured and transparent leadership style, as she explains: “The nature of this role means that you must make fast decisions. If there’s been a data breach, for instance, the media might give you a five-minute deadline for a response. And you have to be open about both the good and the bad. If you’re transparent, that builds your credibility. I make us constantly analyse what’s gone well and where we can improve.”
Mixing strategic and reactive roles
Cafferty’s route into the comms profession was fairly unconventional. She studied international relations at Lehigh University in Pennsylvania before considering going to law school, but had “no idea” what she wanted to do when she graduated.
Leslie Cafferty’s CV
She found an assistant role at InterActiveCorp (IAC) which was transitioning at the time from a broadcaster to an internet business. It was an exciting period to be at the company, led by charismatic media mogul Barry Diller. Cafferty recalls that he was “always doing or saying something that was making headlines”.
IAC had an opening on the communications team, which she thought looked better than answering the phones. After landing the job on her second attempt, she found it “fascinating”, loving the unpredictable nature of the comms function and the fact that it interacts with so many parts of the business.
She rose through the ranks to become director of global communications before moving to market research giant Nielsen in 2011. But she missed the buzz of working in tech and so, when the vacancy at Booking Holdings came up two years later, she seized the opportunity.
For Cafferty, it’s the mix of the reactive and the strategic that really appeals. Although outsiders tend to view Booking.com as a travel business, the comms strategy focuses on positioning it as a tech company. But every member of her 60-strong team has to be ready to drop everything and pitch in whenever something unexpected happens, which has been quite often in recent years. Booking.com must deal with the fallout from events far beyond its control, from the Covid crisis to Russia’s war on Ukraine. How it communicates about such matters is key, she says.
Dealing with a backlash against the business
Cafferty also wants the business to be well known for its strong progressive values. When we speak, the backlash against Bud Light is still reverberating. She believes that the leadership team’s lack of consistency was a huge error for the beer brand.
“They’d made half the world angry [with the original video] and all they did [in response to vehement criticism] was make the other half just as angry,” she explains. “That’s when you have to know your standpoint.”
When she received a call from the company’s lawyers advising her to err on the side of caution with transgender influencers, she ignored their guidance.
“We’ve been working with transgender people for the whole time this company has been in business and we’ll continue to do so, because inclusivity is fundamental to who we are,” Cafferty argues. “We haven‘t faced a backlash but, if that were to happen, my advice would be that we must stand absolutely firm, because it is linked to our values.”
There’s no major decision that this company makes without consulting me and my team
Ensuring a consistent response across a large group is no easy task, of course. When you’re dealing with a workforce of more than 20,000, having everyone understand the parent company’s view on sociocultural issues is “a constant work in progress”. But this is, she believes, central to creating the right culture and ensuring that employees are engaged.
That means including it as part of onboarding and holding annual refresher sessions to remind people what the company stands for. Anyone who’s likely to face the media is trained in its viewpoint and what information they can and cannot disclose.
Nonetheless, mistakes can and do happen. Cafferty recalls a time when one senior leader started deviating from policy by revealing details about the firm’s financial performance in China, for instance. Disgruntled employees have been known to “go rogue” as well, she says, adding that the key to mitigating this risk is to ensure that all staff feel that they’re being heeded, understood and respected.
“If employees are happy and engaged, with clear messages about what can and can’t be discussed, we’re much less likely to face such issues. It’s all intertwined,” Cafferty says.
But unanticipated problems will always come out of the blue and require quick and effective solutions. She learnt one of her biggest – and toughest – lessons during the depths of the Covid crisis. At the time, the whole group was facing an uncertain future as governments around the world imposed stringent travel restrictions. With its HQ in Amsterdam, Booking.com was entitled to state aid. When it took the assistance on offer, it faced an almighty public backlash.
Cafferty describes it as the worst criticism the business has faced during her tenure, admitting that “we had no idea how we were perceived in that market and therefore that there would be this backlash against what’s seen as an American firm accepting Dutch government aid. With hindsight, we shouldn’t have taken it, but at the time there was no travel and we were already having to lay people off. That was a huge lesson for me.”
Raising the profile of the communications function
She cites it as a reason why the communications function should be represented at the top table in more businesses. That’s a more common situation in the US than it is in the UK, but it’s reasonably rare even there for the comms chief to report directly to the CEO, as she does.
That is starting to change, Cafferty says, partly because of the pandemic but also because of the rise of social networks; the increasing public scrutiny that businesses and their leaders attract; and the changing role of the media.
“Gone are the days when you could just push a press release, have someone write a story based on it and that would be that. Relationships matter, so comms has become much more highly valued,” she says. “There’s no major decision that this company makes without consulting me and my team. Most of it has nothing to do with comms, but people recognise that any decision could affect a company’s reputation.”
This means that much of her role entails offering advice in the C-suite and acting as a sounding board for key decision-makers. Cafferty describes her relationship with the CEO and president, Glenn Fogel, as one where they argue “in a good way” every day, debating issues and seeing where they land.
It also means that internal communication is as much a part of the job as external comms. But it isn’t necessarily the more straightforward element, especially when it comes to choosing what subjects to broach with employees.
“There are principles we try to abide by,” says Cafferty, who explains that she and her colleagues will ask themselves a couple of key questions. “First, do we have the right to speak about an issue – does it relate to travel or technology? Second, is that issue relevant in places where we have people? If it isn’t, while we might personally feel passionate about it, it’s not our place [to state an opinion]. And then it’s a case of having debates and using our instincts.”
You get the impression that Cafferty has the instincts to get Booking Holdings through most challenges – and that she probably wins most debates.
