Director of People and Culture, Gasparilla Inn

• Travel + Leisure- 2025 World’s Best Awards: #1 Resort in Florida
• Year-Round Staff: 280

The Gasparilla Inn is one of Florida’s most historic and celebrated private resort destinations, situated on the picturesque Gasparilla Island in the town of Boca Grande along Florida’s Gulf Coast. Founded in 1913, the Inn has welcomed generations of guests and members who return year after year for its timeless elegance, warm hospitality, and extraordinary sense of place. From its landmark yellow Inn building to its pristine Gulf beaches, championship golf, and rich social traditions, Gasparilla is more than a destination, it is a way of life.

The Club and Resort encompass a remarkable range of amenities, including the historic Inn, multiple dining venues, an 18-hole golf course, marina, tennis and croquet facilities, a full-service spa, beach club and a rich calendar of member and guest events. The property is deeply woven into the fabric of Boca Grande’s community, with a long-standing commitment to local philanthropy, stewardship of the island’s natural environment and the preservation of its heritage.

The organization is led by a senior executive team committed to thoughtful, forward-thinking management across all departments. The Director of People & Culture will join the junior executive team and play a central role in shaping the employee experience across one of the most distinctive hospitality operations in the Southeast.

• Travel + Leisure- 2025 World’s Best Awards: #1 Resort in Florida
• Condé Nast Traveler #1 Resort in Florida (Gulf)
• Condé Nast Traveler 2026 Gold List of the Best Hotels and Resorts in the World
• Wine Spectator Best of Award of Excellence
• Listed among Best in State by Golf Digest

• Position reports to:
  Vice President of Human Resources
• Total Employees : 525
• Year-Round Staff : 280
• Seasonal Staff : 245
• H-2B Visa Employees : 150
• Historic Inn, 18 Hole Golf Course, 5 Dining Outlets, Spa & Beach Club, Marina, Retail
• Location :
  Boca Grande (Gasparilla Island), FL

Our mission is to provide authentic, thoughtful hospitality while serving as stewards of our historic property. We do this to create meaningful experiences that enrich the lives of our guests, team and community. United by integrity, excellence and dedication, we honor the traditions that define us as we advance thoughtfully into the future.

The Director of People & Culture is a newly evolved and strategically vital position within The Gasparilla Inn’s junior executive team. This role marks a purposeful shift away from transactional HR administration toward a forward-thinking, strategic people function, one that sits at the intersection of people strategy, organizational development and operational excellence.

The Director will be a creative, solutions-oriented leader who partners proactively with department heads across the property to address workforce challenges, elevate the employee experience and drive meaningful culture change.

The successful candidate will bring both the technical depth of a seasoned HR professional and the visionary thinking of an organizational builder. They will take employee survey and assessment data and convert it into actionable, measurable improvement plans. They will champion the organization’s philanthropic identity and embed it into the employee value proposition.

This is an exceptional opportunity for an experienced HR leader who is energized by transformation, passionate about hospitality culture and inspired by the prospect of building something innovative at one of Florida’s most beloved institutions.

• Lead the evolution of the HR…