Executive Director

Chimney Hill, Southern Vermont’s largest homeowners association and a premier four-season resort community located on 1,200 acres in the Green Mountains near Mount Snow and downtown Wilmington, Vermont, is seeking an experienced Executive Director to serve as its chief administrative and operational leader. Reporting to and partnering closely with the Board of Directors, the Executive Director will oversee all aspects of operations, including staff leadership, financial management, facilities and amenities, infrastructure, and a full-service rental program, while fostering a strong, engaged community of over 550 homeowners. This role requires a strategic and collaborative leader with 5–7+ years of progressive management experience, strong financial acumen, and the ability to build relationships with diverse stakeholders. Responsibilities include budgeting and long-term financial planning, staff supervision, board relations, communications, and ensuring high-quality services across the Association’s extensive amenities and operations. Ideal candidate will have a bachelor’s degree in a related field, along with experience in property or rental management and proficiency with financial and communication systems. Chimney Hill offers a competitive benefits package, including three weeks of paid vacation, an 8% employer retirement contribution, and substantial healthcare support. #J-18808-Ljbffr