Up to the challenge: Sandals' Gary Sadler reflects on more than 30 years in travel

It’s 1988 and a young Gary Sadler has just been told that he’ll never cut it in Jamaica’s corporate sector. Undeterred and looking to take on a new challenge, Sadler secures a job interview with “a little hotel company called Sandals” – and the rest, as they say, is history.

Fast forward to 2019: Sadler is fondly looking back on his time in travel from the confines of a cozy Jamaican restaurant in downtown Toronto. It becomes quickly apparent that he was more or less destined for a role in this industry, where a jovial spirit and larger-than-life personality are among the keys to long-term success.

It’s a very different world from his brief tenure as a top salesperson for a Jamaican furniture distributor.

A new direction

“My managing director told me ‘you don’t fit a corporate profile – you fit tourism. I would strongly recommend that you never consider a job in a corporate, nine-to-five environment ever again in your life.’”

Taking that advice to heart, Sadler applied for and landed a role as a ‘playmaker’ at the then newly-opened Sandals Ochi in Ocho Rios, entertaining travel agents and promoting both the resort and Jamaica as an enticing travel destination, in the months following the devastation of Hurricane Gilbert in 1988.

Sadler’s personality and people skills would soon lead him to a sales position with Sandals and, as the growing resort chain began viewing Canada as a separate market from the U.S., he was eventually tasked with blazing those new trails. Landing in Toronto in July 1992, Sadler would establish both himself and the Sandals brand there over the next 12 months, including the opening of the company’s Canadian headquarters.

However, Sadler says it was his five years in Vancouver that truly shaped his travel career, where the challenge of selling Western Canada’s travel agents on a then-little known all-inclusive Caribbean resort experience was integral to his growth. To that end, Sadler spread the word about Sandals to both trade and consumers in Western Canada and was also instrumental in securing the first charter service in the region to offer direct flights from Vancouver and Calgary to Jamaica.

“Vancouver was the best thing that ever happened to me!” he says. “The biggest challenge was being in Vancouver and handling Alberta, Saskatchewan, the Yukon and Northwest Territories. I enjoyed Western Canada because it was brand-new territory and I just said, ‘here’s an opportunity.’

Challenge accepted

The economic downturn of 2008 was just one of the storms successfully weathered by both Sadler and Sandals, with one of the biggest challenges occurring when Sadler was in charge of the company’s Canadian operations.

Like the travel industry at large, the resort chain was rocked by the economic ripple effect of Sept. 11, 2001; faced with a choice to either recede or expand, Sandals chose the latter and added more BDMs across Canada – a decision which would ultimately prove fruitful and pay dividends down the road.

“Our Chairman (Butch Stewart) believed that we must find a way through it; when life throws adversity your way, there’s usually a way around it,” Sadler recalls. “While everyone else was contracting, we expanded across the board. Our mission was to support the travel agents in the grand scheme of things. Because of that response, it’s the reason why we enjoy such good business in Canada.

That approach to adversity is embodied by Sadler himself, who prefers uncharted waters – and the challenges they bring – to treading familiar territory.

“I don’t shine in a routine or when everything is fine and hunky-dory,” he says. “But the minute that you tell me something can’t be done, you’ve got me so excited because I’m going to prove that it can in fact be done. You can either stay on the sidelines and watch or you can join in and help me.”

Follow the leader

Describing his leadership style as “engaged and involved,” Sadler points to the mentorship he received from Sandals Founder and Chairman Gordon ‘Butch’ Stewart, to whom he attributes his management approach.

His relationship with Stewart goes beyond business, speaking to the strong sense of family at Sandals; when Sadler’s daughter was diagnosed with leukemia in 2013, he says that he was supported every step of the way.

“I put everything on pause and Sandals as an organization was amazing,” says Sadler, who is also a director with the Sandals Foundation, the company’s charitable arm. “Butch called my daughter every Saturday for the six months that she was in the hospital. When you work for a company where the chairman has such a kind soul, everything else is fun and exciting. It’s the key to what you do.”

And as the only Sandals executive in the history of the company to start as a playmaker and work his way up to the position of senior vice-president, Sadler is eager to share his wisdom with others.

“For the sales people, I caution them of one thing: I’ve been there and I’ve done it,” he says. “And because I’ve been there and I’ve done it, I understand that the day-to-day hurdles which I’ve been through as a salesperson, the sales team is going through the same things today.”

“With age comes experience and when youth departs, wisdom proves enough. You just make decisions – even if they’re difficult – without the emotional attachment. My advice to people is that life is short – you’ll have some life-changing moments that make you realize you need to enjoy it for what it is and do the best that you can.”

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