Big Jeff has been a fixture at Waterville Valley for 16 seasons — equal parts ski school technical director, waterpark general manager, and walking encyclopedia of coaching philosophy. But the journey that brought him here started, improbably, with a seven-year-old who could barely get out of bed after his first day on skis.
“I was just beat up,” Jeff told hosts Charlie and Ken during a recent taping of Waterville Unwrapped at The Loft. His mother, he recalled, had never seen a kid his age so wrecked by a day on the mountain. That first outing happened to be at Waterville Valley — a fact Jeff found quietly fitting, given where his life eventually landed. It took three more trips before his father finally lost patience at Sunapee, pointed him toward the chairlift, and said something to the effect of “you’re getting on it.” From that moment, Jeff said, “it was just no turning back.”
Growing up in Woburn, Massachusetts, Jeff channeled that obsession into ski racing, plastering trail maps on his bedroom walls and collecting brochures from every rest stop on I-93. His racing years, though, were humbling. He describes his high school self in terms that are hard to forget: “a baby giraffe on ice.” It wasn’t until his final year of racing at 18, when his body finally caught up with his ambition, that he started putting together solid finishes. That struggle, he says, shaped everything about how he teaches.
The Wife Who Wouldn’t Let Him Skip
After college and a season of ski bumming — first as a snowmaker at Loon Mountain, then out in Bozeman, Montana with a friend — Jeff met his wife, and his westward plans stalled. Back in Massachusetts and working a desk job, he spotted an ad for ski instructor training and signed up, skeptically.
The orientation did not go well. “These people are whacked out,” he told his wife when he got home. “I’m not going back.” The following weekend, a friend offered him seventh-row tickets to a Patriots game. Her response was unambiguous. “The hell you are,” she told him, sending him back begrudgingly to training.
It was there that a veteran instructor who had ties to Waterville Valley pulled Jeff aside and told him to stick close. “The rest is history,” Jeff says. He has spent the 18 years since dedicating his professional life to ski instruction.
Coaching the Coaches
Jeff pursued Level 3 certification with PSIA (Professional Ski Instructors of America) — the highest tier, covering everything from beginner carpet lessons to triple black diamonds — and came to Waterville Valley on weekends specifically because the mountain had four PSIA examiners on staff at the time. He earned his Level 3 on his second attempt and then set his sights on a harder goal: becoming a PSIA educator, which he describes simply as “coaching the coaches.”
That role required a competitive two-day tryout. He didn’t make it the first time. “I didn’t want to think about skiing or teaching” for months afterward, he admitted. But he came back the following season, made the development team, and eventually earned a spot on the Examiner Training Squad — a second competitive gauntlet, this time against the same peers he’d trained alongside.
Now he spends most of the winter traveling across the Northeast — Vermont, Maine, New York, and as far south as Cataloochee ski area in North Carolina — running certification exams and educational events for other ski professionals. He also works with the pros at Okemo in Vermont, a gig that came about through a connection with a PSIA national team member.
Back at Waterville, he designs and runs all instructor training and certification preparation for the mountain’s ski and snowboard staff. The program is free to join, typically running two weekends starting around Thanksgiving — something Jeff mentioned with genuine enthusiasm for anyone curious about getting into instructing.
When Charlie asked what he’s actually teaching at that level, Jeff walked through the layered reality of advanced coaching: technical fundamentals, yes, but also the ability to read a student’s learning style, develop trust, and — critically — know when to stop adding information. “I blow up the whole program,” he admitted, describing the temptation to tack on one more adjustment just as a student starts finding their footing. The golf lesson analogy came naturally: a pro who fixated on his grip from the very first minute never earned Jeff’s trust, and without trust, the learning cycle breaks down.
“The beginner lesson is the most rewarding lesson,” he said, explaining that the gap between zero skiing knowledge and a first successful turn is simply larger than any gain made at an intermediate level. But helping an instructor earn their Level 1, 2, or 3 carries its own reward: “It’s like getting mine all over again.”
An Island, Landlocked by the Forest
Jeff moved to Waterville full-time nine years ago, first renting at the Golden Eagle and then at Mad River, before he and his wife bought a place. For the first two years, she commuted from Massachusetts during the week — a long stretch that COVID ultimately resolved when working from home made the permanent move possible.
He describes Waterville as “an island that’s landlocked by the White Mountain National Forest,” a phrase he said had been rolling around in his head. It’s small enough that waving to people on the road feels normal, and the summers — which he didn’t anticipate loving — turned out to be filled with spontaneous get-togethers and the kind of friendships that don’t happen everywhere. “You just happen to be going somewhere and someone yells out from The Loft, ‘come in here, I’ll give you a free beer,’” he said. That exact scenario may or may not have involved Charlie.
The Other Half of the Year
The bridge between ski seasons came through Whale’s Tale Waterpark, where connections from the ski industry suggested the job as a way to get Jeff to New Hampshire full-time. He arrived expecting something executive-sounding; his first day involved breaking ice out of the lazy river with a pickaxe. Concrete repair came shortly after. Eight years later, he is the General Manager.
The park is open roughly 80 days — mid-June through Labor Day — but takes two to three months to prepare and another stretch to winterize. Jeff loves the chaos of it: the morning meetings that immediately go sideways when staff call out, the radio chatter, the triage of which attractions stay open and which restaurants can keep their kitchens running. “I run around like a maniac until five o’clock,” he said, “and I love every minute of it.”
The two halves of his year fit together better than he expected. As ski season winds down, the waterpark starts pulling at him. As summer fades, the mountain starts calling — usually a couple of weeks before he’s quite ready. “It worked out particularly well,” he said. “In my wildest dreams, I didn’t think I’d be working in the waterpark industry.”
And when asked whether he’d ever leave Waterville Valley? Jeff thought about it and landed on a lottery-winning fantasy: going on tour with some jam bands, catching a run of Phish concerts from a bus, and then coming back home. “I don’t think there’s anything that would really get me to leave the valley,” he said. “But I like my home. I like my home.”
The full episode of Waterville Unwrapped with Big Jeff is well worth a listen — including his wife’s side of the story about losing nearly an entire class of young ski students on her one and only attempt at instruction.