Hospitality Unscripted: Stacy Pilkington on Talent, Culture, and the Art of the Right Hire

Stacy Pilkington didn’t come into recruiting from the outside. She came from 25 years spent inside some of the most demanding properties in luxury hospitality, preopening the Venetian, leading the Rooms Division at the Brown Palace, stewarding the Wailea Beach Resort, and eventually serving as Hotel Manager at the St. Regis. When she moved into executive search, she brought all of it with her.

Now a Senior Recruiting Partner for Global Luxury at Gecko Hospitality, a seven-time Forbes award-winning firm with over 120 recruiters across 80 regional offices, Stacy works with boutique and independent hotels to place leadership that doesn’t just look right on paper but actually fits. Her process is bespoke, her standards are high, and her belief in what boutique hospitality can be runs through everything she does.

The View From the Inside

Stacy’s draw to the luxury and lifestyle end of the market isn’t aesthetic. It’s experiential.

“I came into recruiting after 25 years on the operations side. That background is why I gravitate toward luxury and lifestyle: I understand the standard from the inside. Whether it’s Forbes, Relais & Châteaux, Michelin, Condé Nast, World’s Best, or other top affiliations, knowing the rigor behind these standards aids me in connecting the talent with the property or brand.”

That insider knowledge shapes how she approaches the work, including where the real difficulty lies. “The qualities that matter most in these environments — instinct, discernment, flexibility, emotional intelligence — require a bespoke prescreening process. The challenge lies in gauging alignment through the screening process.”

Beyond the Resume

A resume, Stacy will tell you, only tells part of the story.

“A resume tells you what someone has delivered. It rarely tells you how they lead when no one’s watching, which is what preserves and elevates a boutique property’s culture. Insight and emotional intelligence are crucial components to the conversation.”

Her process goes well beyond credentials. “I ask candidates to walk me through moments that inspired them and challenged them in unplanned ways. Before I present a candidate to a client, I research and learn the property deeply. Excellence means something different at every boutique address.”

A Shifting Profile

The kind of leader boutique operators are looking for has changed, and Stacy has watched that shift happen in real time.

“Command of the operation still matters, but it’s no longer enough on its own. The owners I work with now are looking for leaders who can build culture and retain people, not simply enforce standards. Strategic focus and connection to the internal guests, the people who are doing the work, is not a soft skill anymore. It’s a core requirement.”

There’s another dimension to this shift that she finds equally significant. “There’s also a real shift toward authenticity over polish. Owners want leaders whose hospitality instincts are genuine — that’s harder to find, and far more enduring once it’s in place.”

Recruiting Doesn’t Stop at Placement

Gecko’s partnership with Escoffier and the ESource learning platform reflects a belief Stacy holds from her own years in operations: that getting someone in the door is only the beginning.

“A placement that doesn’t last isn’t really a placement. Having built retention and development plans from the operations side, the difference it makes to satisfaction and profitability is measurable.”

For boutique properties specifically, the stakes are even higher. “It matters even more for boutique properties, which don’t have the bench depth of a larger brand — when a key leader leaves, the culture leaves with them. Development isn’t a nice-to-have there; it’s protection. That’s why a resource like ESource is valuable: it lets us keep investing in someone after the search itself is done.”

What Culture Actually Means

Few words get used more loosely in hospitality than culture. Stacy has a definition she stands behind.

“I’d define culture as what happens in a building on a quiet Tuesday, not what happens during a site inspection — the gap between a standard that’s enforced and one that’s genuinely believed. Culture lives in the hearts of the team, and the guests are invited to participate in it and take it home with them.”

Assessing it during a search requires a specific kind of attention. “I try to understand ownership’s real priorities, not just the stated ones, and I listen for whether a candidate’s language about past teams reflects specificity and care, or only results. It’s evidence I can gather, not a feeling I take on faith.”

What Owners Underestimate

When it comes to building and retaining great teams, Stacy sees a pattern in what boutique hotel owners tend to miss.

“I think owners sometimes underestimate how much a leader’s presence, not just their competence, determines whether a team stays. A flawless track record doesn’t guarantee trust.”

Her message to owners is direct. “Leadership development isn’t a cost — it’s the highest-leverage investment available to them. The team is the product in boutique hospitality, and it deserves to be treated that way.”

Community as a Leadership Signal

Stacy’s career has run alongside years of community leadership work, and she sees a hotel’s relationship with its surrounding neighborhood as more than a values statement. It’s a lens she applies to candidates.

“I’ve seen what a property gains when it doesn’t treat itself as separate from its neighborhood. When I recruit, I look for leaders who already understand that connection. It tends to be a pattern in how someone leads, not a one-time initiative — and it usually says as much about a candidate as any line on their resume.”

Why the Boutique Movement

For Stacy, the boutique movement isn’t a trend she’s following. It’s where she has chosen to put her work.

“Because it still treats people as the product, not the amenity. I’ve worked inside large brand systems and respect what that consistency delivers — and yet, boutique hospitality is where a leader’s judgment and character actually shape the guest experience, rather than being standardized away.”

The moment that keeps her coming back is one she’s seen play out more than once. “I’ve watched what happens when the right leader lands in a small, values-driven property — it compounds in ways that are hard to manufacture at scale. That’s the work I’m grateful to do.”

Stacy Pilkington’s work is a reminder that the best boutique hotels aren’t built on brand standards alone. They’re built on the people who believe in them, and the leaders who know how to protect what makes them worth believing in.