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The arrangement means Trena White, seen here on Dec. 6, 2019, gets to skip the two-and-a-half-hour commute from her home to Page Two’s Vancouver headquarters most days.

Rafal Gerszak/The Globe and Mail

When Trena White co-founded her book publishing company, Page Two Strategies Inc., she was awash with excitement about the business, her newborn son and the charms of life in Vancouver.

But three years later in 2016, Ms. White was grappling with a lack of space in her condo, feeling “fatigued by the city” and yearning to raise her kids in a small community.

She didn’t want to give up her role at Page Two, so she found a way to have the best of both worlds. She became a remote chief executive by moving to the Sunshine Coast, a picturesque B.C. area northwest of Vancouver.

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It’s an arrangement that’s hardly widespread but is becoming more common, according to some in Canada’s business community. An October survey from Statistics Canada revealed almost a quarter of employed Canadians have completed some telework in the 12 months prior, but the report did not narrow down how many respondents were company leaders.

Being a remote CEO has both pros and cons. It can threaten the company’s health and morale, but also gives leaders the flexibility and freedom their personal lives may demand.

The arrangement means Ms. White gets to skip the two-and-a-half-hour commute from her home to Page Two’s Vancouver headquarters most days. She spends only two days a week at the office and her co-founder, Jesse Finkelstein, gives her a place to stay every time she’s in town.

“What makes it work is that I have a co-founder who lives a 10-minute walk from our office and is there on the ground every day,” Ms. White says.

“I also made it really clear from the beginning that people on our team should feel free to do spontaneous FaceTime calls with me or spontaneous phone calls so they can get in touch with me immediately.”

While that allows Ms. White to more easily raise her kids, she admits the distance is tough.

“Sometimes, I miss my colleagues if I don’t see them for too many days and when something big happens or some kind of challenge arises, sometimes I wish I could be there on the ground,” she says.

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“Because we're so far, I can't just hop over there quickly.”

It’s a feeling John Philip Green knows well.

The “chief executive dad” runs CareGuide Inc., a Toronto-based business pairing people with care providers, from Vancouver, where he moved when his wife landed the CEO job at dating service PlentyOfFish in 2018.

Mr. Green was keen on keeping the family together and exploring somewhere new after spending most of his life in Toronto.

“It’s enormously ironic that I would be a remote CEO because what [CareGuide] does absolutely cannot be done remotely,” Mr. Green says.

“We often have nannies, for example, that live in the household or in the case of elder care, it can be very intimate and you couldn't possibly imagine doing that through a computer screen.”

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He has made his situation work by living near the Vancouver airport so he can easily fly to Toronto twice a month. He also hired additional leadership staff and rented a co-working space.

Initially, he had some worries.

“The move actually coincided with us just raising a $6-million Series A investment, so it was a difficult decision,” he recalled.

“The investors went along with it, but they were definitely curious about how it was going to work because it was not a format that they had seen very often.”

If you pop into CareGuide’s Toronto office on a Wednesday, you’ll only find 50 per cent of staff working there because so many workers take advantage of remote opportunities, Mr. Green says.

But it’s far less common for leaders to be remote workers, says Mr. Green, who doesn’t know of many others in a situation such as his.

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Next year, however, he’ll land some high-profile company when Twitter Inc. and Square Inc. CEO Jack Dorsey heads from San Francisco to Africa to work for between three and six months because he says the continent “will define the future.”

Mr. Dorsey has long wanted to create a “decentralized” workplace where anyone can work remotely, but not everyone is a fan of that lifestyle for leaders.

Former Florida Panthers CEO Stu Siegel works from Florida despite his sports analytics company HockeyTech Inc. being based in Waterloo, Ont.

“I would prefer to be on site as a CEO. I don't think it's an ideal relationship,” he says.

“In fact, it's kind of frustrating to me sometimes.”

Mr. Siegel doesn’t like being afar because it can be easy to miss out on office developments such as meeting new clients. To feel engaged, he visits the Waterloo office for a few days every month and uses technology to keep in touch.

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“I have a certain way I like the culture of the company to be and when you’re not there, that’s very difficult to maintain,” he says. “Sometimes, that’s probably my biggest frustration.”

His advice to others mulling over becoming a remote CEO is to focus on building a good team and then ensuring everyone is communicating because “communication is where it breaks down.”

Once you’ve got that on track, Mr. Siegel says “you’ve got to learn how to let go. … That can be the most difficult thing.”

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