Job Description

Position Overview

The Wailea Community Association (WCA), one of Maui’s most prestigious master-planned residential resort communities, is seeking an experienced General Manager (GM) to lead day-to-day operations, long-range planning, and community engagement initiatives. The GM will oversee infrastructure, brand stewardship, financial management, and resident services, while serving as the primary liaison to the WCA Board, local government entities, and community stakeholders. This is a high-impact executive leadership role requiring operational excellence and a deep appreciation for Hawaiian culture and values.

Responsibilities

• Manage all operations of the WCA, including infrastructure, vendor oversight, and member communications
• Serve as liaison between the WCA Board, Wailea residents, commercial stakeholders, and government agencies
• Lead financial planning and oversight, including an operating budget exceeding $4M
• Supervise staff and contractors to ensure high-quality service delivery across the community
• Champion long-range planning and strategic initiatives related to infrastructure, emergency preparedness, and cultural preservation
• Protect and enhance Wailea’s global luxury brand through communications, events, and community partnerships
• Foster a high level of resident engagement, transparency, and trust through proactive outreach and public representation

Skills

• Executive leadership and multi-functional operations management
• Financial acumen, including budgeting, auditing, and reserve planning
• Strong interpersonal, communication, and stakeholder management skills
• Experience in strategic planning, vendor negotiations, and community governance
• Cultural fluency and sensitivity, particularly with Hawaiian values and traditions
• Ability to navigate complex legal, infrastructure, and community systems

Requirements

• 10+ years of experience in nonprofit, resort, property, or community management
• 5+ years in a senior leadership role with oversight of large-scale operations and budgets
• Bachelor’s degree required
• Proven experience managing contractors, staff, and cross-sector relationships
• Familiarity with Maui communities and/or Hawaii-based operations strongly preferred
• Track record of effective board engagement and brand management in a public-facing role

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