2024 NSAA Lifetime Achievement Award: Kenny Hess, A Small Ski Area Big Thinker

Kenny Hess was on a familiar trail toward ski industry leadership. A couple chance encounters with work connections collided with his ski area background to put him on that path. While the start of his story has all the trappings of a classic ski career commencement — complete with "in it for the free ski pass while I got my degree" — Hess diverged in at least one significant way. He spent almost the entirety of his career at Massanutten Resort, Va., a place he thought was in his rearview after graduating.

Now about to step down from his current post as director of sports and risk management and embark into retirement this summer, Hess is proud to have been able to develop a career out of a passion for both the sport and industry.

"In hindsight, doing that while remaining at a small ski resort (in Virginia of all places) is surreal," he reflected. "Being part of the transformation of what Massanutten was in 1980 to what it is now has been very gratifying."

By all measures, Massanutten is considered a small ski area. But at 6,000 acres, the operation and property it sits on are far from it. During his time at the helm, Hess played an integral role in Massanutten's success, developing new skiers and riders, and bringing lodging and recreation amenities to life, according to Jay Roberts, executive director for Wintergreen Property Owners Association.

He and Hess crossed paths early in both their careers, serving as patrol directors in the Southeast at the same time. Roberts commended Hess on 44 years — "a big number, even bigger when you take into consideration the volatility of the winter sports business in the Southeast."

"It takes grit, smarts, a commitment to the industry and … the lifestyle to be successful," Roberts said. "Over his 40+ year career, Kenny … embraced mountain biking when many were still trying to figure it out. He operated snow tubing at a level very few could achieve."

The list of amenities and upgrades Kenny had his hands in goes on and on, according to Roberts, and included chairlift upgrades, new slopes, waterpark, expanded snowmaking, lift loading conveyors, ice skating, terrain parks, zip lines, and ropes courses.

"Through the ups and downs of resort operations and ownership challenges, Kenny never wavered and he never left," Roberts added. "He simply kept improving."

Real World, Real Job

Hess worked as a part-time lift operator and then a ski patroller while earning his BBA in marketing at James Madison University. It was the early 1980s, and although they didn’t say gap year back then, Hess was looking to take some time before entering the "real world" after graduating. The first of his right place, right time run-ins happened on a spring trip to Vermont in "one of those random moments getting off the lift and seeing someone you know," he said.

That someone was a patroller friend who was working at Sugarbush. A couple of runs turned into an invitation to join their ski patrol, under the leadership of Blaise Carrig, and Hess took Sugarbush up on the offer the following season. Carrig remembered Hess as someone who possessed the skills of a strong ski patroller, and then some.

"He was impressive from the get-go," said Carrig. "He also had a really good head on his shoulders. You could tell, even at that point in his career, he had a bigger view of the business [and] that he was a lot more well-rounded in that respect. He also got the guest service component, which, back in those days, not a lot of ski patrollers did."

"I was never surprised that he went on and became the leader that he did because I think he exhibited a lot of those characteristics really early on," continued Carrig.

Even so, Hess headed back to Virginia for a "real job" a year later — an effort to placate his parents who paid for his education. But it was only a few months before another chance meeting would once again change Hess’ course. This time, he bumped into some friends from Massanutten at a ski binding clinic.

"I was managing the ski/golf department in a Northern Virginia retail store, and my previous boss from Massanutten called me and asked what I was going to do for the winter," said Hess, who had been contemplating moving back to Vermont. "We met, and he gave me the choice of managing Massanutten’s ski shop or managing the patrol. I chose the patrol director job for the season and was kept on full time, year-round that spring."

Being that Hess was one-third of the summer staff, which at the time consisted of him, the GM and the marketing director, his involvement quickly ballooned to lift and slope maintenance, rental shop, risk management, ski shows and wherever else he could lend a hand. Hess’ perspective-broadening responsibilities didn’t end there. In the lead-up to his current position, he served as director of business operations overseeing ski, tubing, adventure park, mountain bike, golf (two courses), waterpark, aquatics (five pools), spa, recreation (two facilities) and risk.

"I was getting spread pretty thin," he admitted. "When the previous ski area manager decided to step back, we restructured, allowing me to focus on ski, tube, adventure park, mountain bike, golf and risk, which is where we are now."

Massivenutten

Hess’ title today is unique to Massanutten and his growth there, which reflected the ever-expanding resort around him. At another ski area, he would probably be GM or COO, but he’s never been lured by what lies beyond his property’s boundary. For one, Hess wasn’t all that interested in being siloed into one corporate ladder or another. Sure, he could have moved on to bigger mountains, deeper snow and better skiing, but his professional prospects were always met right where he already was (not to mention that’s where his wife was also building her career).

"Kenny could easily have gone on to hold important positions anywhere in the country," said Roberts. "He certainly has all of the knowledge, commitment and experience to do any of those jobs. He chose to stay in the Southeast, and we thank him for that."

Hess also recognized the drawbacks in those shiny new job opportunities when weighed against the stability he enjoyed at Massanutten.

"We were never really in a position … when we had a poor snow year, a poor weather year or poor business year, that it was like, 'Alright, well, which middle managers or which entry level people are you going to have to lay off?' Hess pointed out. "I saw that happening to some of my peers where they'd move somewhere … 'I just got laid off because we had a crap year.'"

While skiing is foundational to Massanutten history and remains an important anchor point for the business, it is one amenity among many, according to Hess. Variety, he added, takes the sting out of a challenging season. At a certain point, skiing was no longer driving the engine, where "everything didn't live and die on seasons pass sales and daily ticket sales, ski lift ticket revenue," he explained.

Quintessential Collaborator

In addition to retiring with an NSAA Lifetime Achievement Award on his shelf, Hess was also inducted into the Massanutten Hall of Fame. The Champion Award recognizes tireless leadership and considerable contributions to the resort, the community and the mountain sport industry as a whole. Apart from championing major change at Massanutten, this award also acknowledged Hess’ impacts on ski patrol employee and volunteer relationships, and that he introduced safety and risk management as a priority. As part of that, Hess helped steer Virginia’s Winter Sports Safety Act though the legislature.

"Virginia was one of the few ski states that didn't have a skiers responsibility act or skier safety act, and Virginia is pretty difficult to do business in. The way that Virginia law works is everything goes to a jury trial," Hess said, adding that those juries weren’t apt to uphold the state’s contributory negligence rule that prevented negligent plaintiffs from collecting damages. "We just found a way to codify what we're responsible for and what they're responsible for. Getting that through in a state that only has four operating ski areas … was [an] interesting learning experience for me. I was also able to get tubing specifically excluded from the Virginia amusement device regulations because at one point, tubing was considered an amusement device."

NSAA’s Byrd offered more evidence of Hess’ strength on the risk and safety front, recounting a 2016 chairlift incident at a nearby ski area. When Hess got word of what happened, he looped in Byrd and Berry in near real-time and helped galvanize the industry response. To Byrd, Hess was the "quintessential industry collaborator," who kept NSAA apprised of the Southeast’s status. That willingness to share is vital and rare, in Byrd’s book, with only a small handful of other industry leaders who came to mind as being out front of situations the way Hess was.

Roberts agreed and mentioned that Hess openly shared his ideas, new initiatives and goals. "Kenny was a regular source of inspiration for me, and he welcomed calls to discuss our similar challenges," Roberts said. "His easy ability to laugh when sharing stories of the often chaotic business was welcomed relief. Kenny fully understood success for Massanutten was tied to success of the region and the sport. As a result, he served in numerous leadership roles to help guide all of our success."

Even after Hess closes out more than 40 years at Massanutten, his brand of proactive, solutions-oriented resourcefulness will live on with MountainGuard as the beneficiary — he has plans to do some consulting work for the insurance company, helping out with operations visits. This will, of course, also satisfy another big aspiration for Hess’ retirement: lots of skiing. To go along with it, Hess is looking forward to more time mountain biking, golfing and grandparenting.

For now, he’s helping ensure a smooth transition at Massanutten and no doubt imparting nuggets of wisdom like these words for his younger self, if time travel permitted: "I’m not sure I would have listened, but I’d probably say, 'If you manage your team well, everyone around you will look like rock stars, and don’t get caught up in who gets the credit.'"