The rise of the digital nomad boss

Could you run a business effectively while travelling abroad, possibly several time zones away from your team? Some adventurous senior decision-makers reveal how they’ve been making things work from afar
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For months, members of Augustin Delaport’s team enjoyed a running joke. Each time he was due to have a video call with them, they would try to guess what kind of landscape they would see behind him on their screens when he logged on. 

“It could have been a fjord, a mountain, a beach or a forest,” he says with a laugh.

That’s because Delaport spent more than 15 months travelling Europe in a camper van while holding down his job as vice-president of product at, a French tech company. Along with his wife, two young children and cat, he visited 15 countries across the continent, from Portugal all the way up to Norway. 

Augustin Delaport’s office during his extended European tour

Each Monday, the tour party would set themselves up in a new campsite for the week, with Delaport working on his laptop on a folding table next to the van. He reserved weekday hours after 5pm and weekends for “pure creative time” with his family, often enjoying outdoor pursuits such as hiking and swimming. 

“It was a very simple routine, but always in a different location,” he says. 

The adventure ended only when his son wanted to go back to school. The family duly returned home to Paris last November.

This kind of idyllic location-swapping lifestyle has never been more accessible to white-collar workers, thanks to the lockdown-driven boom in remote working. Digital nomadism has taken off to the extent that some countries have established special visas for remote workers, while local communities in some particularly popular destinations have protested against what they see as a destabilising influx of nomads

Until recently, it was seen as the preserve of young creative freelance workers who didn’t care much for traditional career advancement. But that picture is looking increasingly out of date. Nomad List, a resource for remote workers travelling the world, reports that its typical user is aged between 30 and 40, with more than a third earning more than $100,000 (£79,000). A large minority (43%) are in full-time employment. That includes a growing number of business leaders who are embracing flexible policies to take extended international trips or even relocate to sunnier climes thousands of miles from their companies’ HQs.

The digital nomad CEO

Jeff Maggioncalda is the CEO of Coursera, a Californian tech firm that provides an online learning platform. He decided to switch the company’s 1,400 employees to a permanent remote-first model after the first Covid lockdown.

Not only was this new policy good for recruitment and retention; Maggioncalda also used it to indulge his own wanderlust. Although he’s based in Silicon Valley, he is “never usually in one place for longer than a few weeks”.

In the five months to March, he worked in 35 cities. That included a six-week, eight-country trip across Europe and the Middle East at the start of this year. He also spent time in India.

While this lifestyle might sound idyllic to those seeking adventure, Maggioncalda warns that “it’s not always easy”. Sometimes he works six days a week or from 8am to after midnight to keep up with team members working in other time zones. He has spent less time exercising and his sleep quality has declined, while he sometimes misses his family and friends in the US.

But Maggioncalda is effusive about the benefits of this way of life and work. Meeting so many new people face to face and having a wide range of experiences give him valuable insights into Coursera and its customers, he says. Being a nomad also enables him to “engage with the people and beauty in this world. I love learning about evolution, history and culture. I can’t imagine a more thrilling way to learn than by seeing it at first hand and living it.” 

Not all companies are so open to having globetrotting senior executives, of course. In most countries, including the UK, overseas work comes with legal and regulatory considerations that many businesses would rather not trouble themselves with. 

A 2022 survey by Deloitte found that, while 66% of employers permitted employees to work remotely in the same country, the proportion dropped to 35% for staff seeking to work long spells overseas. Of those that didn’t have cross-border employment policies in place, 60% limited the number of days that employees were able to spend abroad. 

Managing a team as a digital nomad

Student Beans is one UK firm that’s made a significant effort to accommodate employees’ extended travel plans. The company‘s policy is that people can work from anywhere in the world they choose for up to six months. Requests for longer relocations are reviewed on a case-by-case basis.

For Will Weeks, head of brand and communications at Student Beans, it was the push he needed to move back to his native Sydney from London. To many, it would seem unfeasible to lead a team of 32 people, four of whom report directly to him, on a 12-hour time difference.

Weeks manages this by splitting his working day in two. He gets through a few hours of focused work in the morning, has a long break and then logs back in again between 8pm and midnight to match his team’s schedule.

“Not having the traditional eight hours at a desk is what seems to work for me,” Weeks says. “It allows me to have a more active lifestyle because I can get out to the beach or go for a run when the sun is shining. When others are sitting on the couch and watching TV, that’s when I work.”

‘When others are sitting on the couch and watching TV, that’s when I work’

He also believes that the arrangement has made him a better manager. Whereas he might have relied before on being able to talk to colleagues at any point of the conventional working day, he now focuses on planning so that his team members can make more of their own decisions.

Weeks adds that ensuring that everyone knows exactly what they are working towards each quarter has helped him to become more disciplined and strategic. Using a more command-and-control management style would have been out of the question, he adds, stressing that “communication is the thing that makes this work”.

Ishveen Jolly, the founder and CEO of OpenSponsorship, also leapt several time zones after the Covid crisis. She runs the US-based influencer agency from London, flying to New York or Los Angeles when required.

While the young company’s remote working policy has helped it to attract talent and maintain a global outlook, she admits that it’s been difficult to keep up the strong sense of “camaraderie” she’d worked hard to build. 

After a difficult meeting, for instance, Jolly has to spend “a lot more time doing one-on-one meetings afterwards to see how people are feeling. That’s because I’m not physically there to put my arm around someone and say ‘that was tough, but we’re good’.”

Could such disadvantages start to outweigh the benefits? Data from LinkedIn indicates that the number of remote job openings had fallen from its peak by the end of 2022, while many employers are ushering staff back to HQ amid fears that productivity is suffering.

But these trends might not hold leaders back. For instance, Groupon’s new interim CEO, Dušan Šenkypl, plans to run the Chicago-based company from the Czech Republic. 

Senior executives have always tended to favour a globetrotting life, after all. Why not add in a little leisure along the way? Delaport, for one, would love to get back on the road. 

“There are zero regrets from that experience,” he says. “If the kids were up for it, we would go again immediately.”