The Leadership Paradox Facing North American Ski Resorts: Why This Season Reveals Your Succession Gaps
Enzo Lee, Profile Search International
Mid-December at any ski resort tells you everything you need to know about leadership. Lifts are spinning, terrain is opening, holiday crowds are arriving, and your executive team is either thriving or barely hanging on. This moment—when operational demands peak and strategic thinking takes a back seat—is precisely when smart resort operators start planning for next year's leadership transitions.
Yet across North America's ski industry, a troubling pattern has emerged: resorts that appeared operationally sound last spring are now scrambling to fill critical leadership gaps, while those who planned succession strategically are navigating this season with confidence and depth.
The New Reality of Resort Executive Recruitment
The appointments announced in recent months tell a revealing story. Burke Mountain Resort named industry veteran Gabe Porter-Henry as General Manager in December, while Powder Mountain elevated internal candidate Brandi Hammon to President after she proved herself as Chief Revenue Officer. Red Lodge Mountain brought in Jean Mikulas with over 25 years of ski industry leadership experience. Vail Resorts announced Celeste Burgoyne would join as Executive Vice President and Chief Revenue Officer in January 2026, pulling talent from outside the ski industry with her lululemon background.
These moves weren't made during the off-season—they were announced mid-winter because succession planning and executive recruitment don't pause for peak season. In fact, the best time to address leadership gaps is when they're most visible.
Why Traditional Succession Planning Fails Resorts
Most ski resorts treat succession planning as an emergency response rather than a strategic process. A General Manager announces retirement, a VP of Operations accepts a position elsewhere, or a Chief Revenue Officer burns out mid-season, and suddenly the board is scrambling to find replacement talent during the busiest operational period of the year.
This reactive approach creates three critical problems:
First, the talent pool shrinks dramatically when you're recruiting on short timelines. The strongest executive candidates—those currently thriving in leadership roles at other resorts or in adjacent industries—typically require 6-12 months' notice to consider transitions. When you're operating on 60-90 day timelines, you're automatically excluding the best talent from consideration.
Second, rushed executive searches lead to costly mis-hires. Industry research shows that 40% of executive transitions fail within the first 18 months when proper cultural fit and operational alignment aren't thoroughly assessed. For a resort General Manager earning $180,000-250,000 annually, a failed hire can cost the organization $500,000-750,000 when you factor in recruitment costs, severance, operational disruptions, and the expense of re-hiring.
Third, reactive succession planning signals organizational instability to both internal teams and the broader industry. When talented mid-level managers see leadership transitions handled poorly, they begin exploring opportunities elsewhere. The best operations directors, food and beverage managers, and mountain managers—your future executive talent—start updating their resumes.
The Housing Crisis Compounds Leadership Challenges
Even when resorts identify strong executive candidates, a new barrier has emerged that's reshaping the entire recruitment landscape: housing affordability at every level, including six-figure executive roles.
Steamboat Springs recently made national headlines when two qualified candidates turned down a $167,000 Human Resources Director position because they couldn't find affordable housing. The local hospital has positions for highly-paid physicians that have remained unfilled for over two years due to housing constraints. One hospital president noted, "Even your top earners with physician pay ranges are sitting in my office saying, 'I don't know if I can afford to live here'".
This isn't just a Steamboat problem—it's reshaping executive recruitment across Aspen, Jackson, Park City, Truckee, Sun Valley, and every other resort market where real estate prices have disconnected from local incomes. Resorts that once competed purely on compensation packages, career growth opportunities, and lifestyle benefits now must address housing directly or lose executive candidates to markets where six-figure salaries translate to reasonable housing options.
Forward-thinking resorts are responding by including housing stipends in executive compensation packages, securing master leases on rental properties for leadership teams, partnering with local housing authorities on workforce housing initiatives, or even developing their own executive housing solutions. Aspen Skiing Company pushed forward with its $18.5 million Hub at Willits employee housing project, adding 150 beds to bring their total employee housing to 820 units. These aren't amenities—they're now recruitment necessities.
What Successful Resorts Do Differently
The resorts navigating leadership transitions successfully share several common practices that separate them from organizations constantly firefighting executive gaps:
They Plan 18-24 Months Ahead: When Vail Resorts announced Chris Jarnot would step down as Executive Vice President after 34 years with the company, they simultaneously announced the creation of three new regional leadership roles and identified internal successors for multiple positions. This wasn't reactive—it was strategic succession planning that gave the organization time to communicate changes, transition responsibilities, and maintain operational continuity.
They Build Internal Benches: Powder Mountain's promotion of Brandi Hammon to President demonstrates the value of developing internal executive talent. She had proven herself in a demanding Chief Revenue Officer role, understood the resort's culture and strategic direction, and had earned credibility with both the board and operational teams. Internal promotions reduce hiring timelines, minimize cultural integration risks, and signal growth opportunities to ambitious mid-level managers.
They Embrace Flexible Leadership Models: The outdoor industry is increasingly adopting fractional and interim executive arrangements that provide C-suite expertise without full-time commitments. For resorts facing specific transformational challenges—new ownership transitions, major capital projects, revenue management system implementations, or organizational restructures—fractional executives can deliver outcomes-based leadership while the organization develops permanent solutions.
They Think Beyond Traditional Ski Industry Talent: Vail's appointment of Celeste Burgoyne from lululemon represents a broader trend of bringing executive talent from hospitality, retail, technology, and consumer goods industries into resort leadership. While deep ski industry experience remains valuable, resorts are recognizing that exceptional executive capabilities—strategic thinking, change management, digital transformation, team building—often transfer effectively across industries when paired with proper onboarding and support.
Best Practices for Mid-Season Leadership Assessment
December's operational intensity provides the perfect diagnostic opportunity for evaluating your leadership team's readiness for future challenges. Ask yourself:
Which executive roles would create immediate operational crises if suddenly vacant?
Are your high-potential mid-level managers receiving mentorship and development for future executive responsibilities?
Does your compensation structure compete effectively with both resort industry peers and adjacent industries recruiting similar talent?
Have you addressed housing accessibility for executive candidates considering your market?
When did you last conduct formal succession planning discussions with your board?
The resorts that will thrive over the next decade aren't necessarily those with the most terrain, the biggest snow totals, or the closest proximity to major airports. They're the organizations that build deep leadership benches, plan succession strategically, and recognize that executive talent is the foundation upon which operational excellence is built.
Taking Action Now
If your resort hasn't conducted a formal succession planning process within the past 18 months, this season's operational realities should serve as your catalyst for change. The executive talent you'll need for the 2026-27 season and beyond isn't sitting idle waiting for your job posting—they're currently leading successful operations elsewhere and will require strategic recruitment, compelling value propositions, and sufficient transition timelines.
The resorts announcing leadership appointments in December didn't start their search processes in November. They began identifying candidates, building relationships, and structuring offers months earlier, positioning themselves to secure top talent when others are still hoping operational band-aids will solve structural leadership gaps.
Your competitors are already planning for next year's leadership team. The question is whether you'll join them in strategic succession planning or continue operating reactively until the next executive transition crisis forces your hand.
Profile Search International specializes in executive recruitment for ski resorts and outdoor brands across North America. We help forward-thinking organizations build strong leadership teams through strategic succession planning, comprehensive candidate identification, and proven placement processes. Contact us to discuss your leadership planning for the 2026-27 season and beyond.