The Organization

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.

Awards Received by the Property Include:

• 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

The Gasparilla Inn

• 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

Mission Statement

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.

Position Overview

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.

Responsibilities

Strategic HR Leadership & Business Partner Model

• Lead the evolution of the HR department from a transactional HR function to a proactive, consultative HR Business Partner model serving all departments of the Inn and Club.
• Serve as a trusted strategic advisor to department heads and the junior executive team on workforce planning, organizational effectiveness and people related decision making.
• Identify and champion creative process improvements across HR operations, bringing forward-thinking solutions and best practices from the broader hospitality and SHRM communities.
• Join the junior executive team and contribute meaningfully to cross-functional leadership conversations, planning and organizational priorities.

Culture, Engagement & Assessment

• Own the organization's employee engagement and culture assessment process, administering surveys, analyzing results and translating findings into well-structured action plans.
• Collaborate closely with department leaders to implement action plans that address identified gaps and reinforce organizational strengths.
• Champion an inclusive, vibrant and values driven workplace culture consistent with The Gasparilla Inn's legacy and community identity.
• Track and communicate measurable progress on culture initiatives to the executive team.

Benefits Design & Improvement

• Conduct a comprehensive review of current employee benefits offerings and lead the development of a roadmap for meaningful improvements that enhance recruitment, retention and employee well-being.
• Research competitive benefit structures within the hospitality and private club sector and benchmark accordingly.

H-2B Visa Program Oversight

• Provide oversight, guidance and strategic direction for the H-2B visa program, with an eye toward eventually bringing key aspects of the process in-house as organizational capacity grows.
• Partner with and actively support the internal staff member currently developing visa expertise, building institutional knowledge over time.

Philanthropy & Community Engagement

• Serve as a steward of the organization's philanthropic identity, coordinating employee volunteer programs, charitable giving initiatives and community partnerships that reflect the Gasparilla Inn's deep roots in Boca Grande.
• Build a framework for employee driven philanthropy that strengthens engagement, pride and a sense of shared purpose throughout the workforce.

Skills, Background & Personality

• A genuine passion for people and a deep belief that employee experience drives guest experience, this individual understands that culture is a competitive advantage.
• A creative and innovative entrepreneurial mindset with the ability to identify problems, design solutions and execute with discipline and follow through.
• Highly energetic and self-motivated; excited by the opportunity to shape and elevate the department rather than simply maintain it.
• Emotionally intelligent with the ability to build trust across all levels of the organization, from seasonal line staff to the executive team.
• A data-oriented thinker who can move from assessment insights to structured action plans with clarity and purpose.
• An excellent communicator, written and verbal, able to navigate sensitive conversations with professionalism, empathy and directness.
• A values driven leader inspired by the organization's philanthropic mission and proud to represent it in the broader community.
• Comfortable leading change in a distinguished institution that honors tradition while embracing the future.
• An authentic presence that makes employees feel seen, heard and valued.

Requirements

• A Bachelor's degree in Human Resources, Business Administration, Hospitality Management or a related field.
• SHRM-CP or SHRM-SCP certification strongly preferred; active engagement with SHRM frameworks and HR industry trends.
• 4-5 or more years of progressive HR experience, including a HR Business Partner Model or equivalent role.
• Prior experience in hospitality, private clubs, resorts or a comparable multi-faceted service environment.
• Proven ability to design and implement HR transformation initiatives.
• Experience translating employee engagement or culture assessment results into structured, measurable action plans.
• Track record of meaningful improvements to employee benefits programs.
• Familiarity with H-2B visa processes and seasonal workforce management; direct H-2B program experience is a meaningful plus.
• Demonstrated experience leading and developing HR teams, including HR managers and coordinators.
• Working knowledge of employment law, FMLA, ADA, FLSA, EEOC compliance and multi-state HR regulations.
• Strong data analysis skills and proficiency with HRIS platforms.
• Established involvement in philanthropic or community engagement initiatives.
• A career path marked with stability, professional achievement and upward progression.
• Exceptional written and verbal communication skills, with the ability to engage effectively across all levels of the organization.
• Impeccable and verifiable references. All candidates will be subject to a thorough background check.

Competitive Compensation

The Inn offers an attractive and competitive compensation and benefits package.

To be Considered

To be considered for this outstanding opportunity, qualified professionals are encouraged to submit a compelling cover letter addressed to Mr. Brent Cross, President and General Manager of The Gasparilla Inn, along with their resume and professional references. Your cover letter should speak directly to your HR leadership philosophy, your experience driving organizational culture change, and what draws you to both this role and the unique community of Boca Grande.

All materials received will be kept in the strictest confidence. Candidates who meet or exceed the qualifications outlined above should submit their application to:

Thomas J. Noyes, CCM, CCE
Principal
tnoyes@gsiexecutivesearch.com
941-525-3211

Mary Kate Addison, SHRM–CP
Principal
Marykate.addison@gsiexecutivesearch.com
469-265-1326