Position{{:}} Executive Director

Organization{{:}} Chimney Hill Homeowners Association

Website{{:}} www.chimneyhill.com

Location{{:}} Wilmington, Vermont

Job Type{{:}} Full-Time, onsite

Compensation Range{{:}} $90,000-$110,000 (commensurate with experience)

About Chimney Hill

Chimney Hill is Southern Vermont's largest homeowners association and a premier four-season resort community. Situated on 1,200 acres in the Green Mountains—just minutes from Mount Snow and downtown Wilmington—Chimney Hill offers exceptional amenities and services to a vibrant community of over 550 homeowners.

Amenities include tennis and pickleball courts, an outdoor skating rink, extensive trail systems, a fishing pond, and a fully equipped clubhouse featuring indoor/outdoor pools, fitness facilities, and family-friendly spaces. The Association also manages its own infrastructure, including a water treatment facility and miles of private roads, supported by a dedicated professional staff and a full-service rental program.

Position Overview

The Executive Director serves as the chief administrative and operational leader of the Association, working closely with the Board of Directors to ensure the effective management of Chimney Hill's operations, staff, amenities, and services. This role is responsible for fostering a strong community, maintaining high-quality services, and ensuring the long-term sustainability of the Association.

Key Responsibilities

Lead and manage all aspects of Association operations, including staff, programs, facilities, and owner relations
Hire, supervise, and evaluate staff; oversee employee benefits and personnel matters
Oversee financial management, including budgeting, financial reporting, and long-term financial planning
Ensure compliance with financial policies and assist with annual audits
Serve as the primary spokesperson and representative of the Association to homeowners, guests, and the broader community
Collaborate closely with the Board of Directors; support leadership in policy development and implementation
Prepare for and participate in Board meetings, including agenda development and reporting
Provide oversight of the rental program, including operations, marketing, guest services, and financial performance
Manage communications, including social media strategy and homeowner engagement
Act as liaison to legal counsel and external partners
Foster a collaborative, respectful culture between the Board and staff

Qualifications & Experience

Bachelor's degree in Business, Public Administration, Facility/Recreation Management, or a related field preferred
5-7+ years of progressive management and supervisory experience
Strong financial acumen, including budgeting, financial reporting, and accounting systems
Demonstrated leadership skills with the ability to think strategically and plan for the future
Proven ability to build and maintain relationships with diverse stakeholders, including boards, staff, and community members
Excellent organizational, communication, and analytical skills
Proficiency in Microsoft Office and experience with computerized accounting systems
Experience with social media and content management
Rental or property management experience preferred
Ability to obtain a Class 3 water operator's license within 24 months

Benefits

Three weeks of paid vacation
Employer contribution of 8% of base salary to retirement IRA
Substantial healthcare cost contribution

Gallagher, Flynn & Company, LLP

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Executive Director - Chimney Hill