Much has been made about Whistler Blackcomb’s 50th anniversary this year, but little fanfare has been spent on Bobby Swain’s third decade at Cypress Mountain.
While the top bosses at big recreation organizations aren’t generally known as spotlight dodgers, the president and general manager of Cypress Mountain maintains a behind-the-scenes style. Yet despite his deliberately low profile, Swain’s accomplishments – such as helping direct Cypress Mountain’s successful transformation from local Hollyburn hill to marquee Olympic destination – are outsize.
Cypress has recently opened for the season and is hoping to rebound from last year’s bare-slopes writeoff. It has added five more snow guns this year and has plans to extend snow-making on the mountain in the near term.
Entering his 31st year on the mountain, Swain is not focused on a career retrospect but instead is fine-tuning a forward-looking strategy that will see Cypress Mountain through to 2025. Swain wants the ski area to be more sustainable, both environmentally and economically. The twin goals are for Cypress Mountain to be on the “right side of the environmental ledger” while providing a more affordable skiiing experience to Lower Mainland families.
“When I see a mom or dad coaching their children downhill or clunking up the stairs with their ski boots it just kills me,” said Swain, 63. “It’s a beautiful thing that inspires. It makes everything worthwhile. I really want to make skiing more affordable so I can see more parents with kids. That’s the future I want to leave.”
When asked to describe the understated Swain, some throw out comments like “He flies under the radar.” But those same people also note that profile isn’t everything.
CNL Financial Group, the owner of Cypress Mountain as part of a real estate income trust package, has created or acquired companies with more than $33 billion in assets. So, they’ve been exposed to a pretty large executive class.
“[Swain] is one of the most capable and accomplished in our group of 15 GMs that run our resorts,” said CNL senior managing director Stephen Rice, who oversees the company’s recreational and retirement properties. “He just exhibits the traits you look for in senior leadership. He has the support and respect of his staff, first and foremost, which allows you to have a team. Because no matter how good a GM is, [he is] only as good as the people who are working for him.”
Kevin Webb, president of North Construction, is a well-known ski resort civil contractor who has overseen multimillion-dollar projects at many resorts in Western Canada. Swain “lives and breathes that mountain” more than most, said Webb.
“You’ve got to have the passion to be in this business,” Webb said. “Pretty much all the mountain managers have that but definitely none of them invests as much time as Bobby does.”
Swain’s ascent to the top of Cypress Mountain was a journey that began 900 metres underground when, as an 18-year-old, the Sudbury native worked as a hard-rock driller at Inco’s underground nickel mine.
“I figured out what I didn’t want to do in very short order,” Swain recalled.
So he got his civil engineering technology degree and headed west. When he ended up in Vancouver at an engineering consultancy designing mine sites, Swain found himself largely living in the field at a Tumbler Ridge coal project. As in his underground days, Swain didn’t like his working environment.
In 1984, he switched career tracks, giving up surveying for large civil construction projects and signing on as food and beverage manager of Cypress Mountain, the same year the resort was purchased by Cypress Bowl Recreations Ltd.
“It was really Cypress’ first year,” Swain said. “I had absolutely no experience. I wasn’t a big skier then either.”
“But I both knew and liked the owner,” he added, chuckling. “It’s just something I decided to do.”
And he’s never left. Early on at Cypress, the manager once responsible for overseeing chili and hamburgers decided to add something audacious to the menu: a new chairlift.
Swain had walked to the summit of Mount Strachan, where the view from the top revealed a business opportunity for a new lift. He oversaw the purchase of an existing lift from Apex Mountain Resort and took care of everything else with an assembled team, from transport and site preparation through to final build.
“The first time the GM looked at the whole lift was when it was done,” Swain said. “He didn’t have to be involved. We took care of the whole works. We didn’t know what we were getting into and it took a lot of hours and planning to get it done. Most importantly, with the addition of Sky Chair, our business doubled in that one year.”
Swain’s early hands-on planning and hard work still hold true today, Rice said.
“It kind of complements his personality that he’s not afraid to jump in and get his hands dirty on no matter what the priority of the moment might be,” Rice said. “It just speaks volumes. People just respond to that. He’s always out there, visible and making a difference.”
Swain has been involved in all of Cypress’ many facilities, snow-making and terrain improvements over the years, both as planning and development manager and in the current role he’s held since 2010. The majority of capital projects materialized under the ownership of Boyne Resorts (2001-06) and current owner CNL Lifestyle Properties Inc. And, of course, Cypress’ selection as a venue for the 2010 Winter Olympics spurred additional investments and many new builds.
Swain has consistently shown a tactful and honest approach in his leadership role at Cypress, much like the one he maintained in team sports such as basketball growing up. Swain wasn’t a win-by-intimidation player. His wins were built on the foundation of his teammates’ respect.
“I was always captain of my team back in high school and college,” he said. “I wasn’t a loud guy. I was lead-by-example, and if there were issues I would try to sort them out behind the scenes. I never strived to be a leader of any team I was on. It just happened naturally.”
Swain expects to publish Cypress Mountain’s 2025 goals early next year. He may very well still be at Cypress to see the strategy through to its end date.
“In 30 years I’ve never even thought I was going to work. Coming out here and doing whatever role I was doing, it has never been a workday.” •
