# Executive Director - Chimney Hill

> Gallagher, Flynn & Company · Wilmington, United States · Full-time · Posted 2026-05-05

**Salary:** USD 90,000–110,000

**Workplace:** on_site

## Description

Position: Executive Director

Organization: Chimney Hill Homeowners Association

Website: [www.chimneyhill.com](https://www.chimneyhill.co)

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

## Apply

[Apply at Gallagher, Flynn & Company](https://apply.workable.com/gallagher-flynnand-company/j/50FD917050/apply)

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