Executive Director

Retreat Farm; Brattleboro (VT); On-site; USD 125,000 - 140,000; Full time

Benefits offered by this job

Health insurance

Vision and dental insurance

SIMPLE IRA with 3% employer matching

Generous paid time off

Staff discount at Retreat Farm Market

Job summary

Retreat Farm in Brattleboro, Vermont seeks an Executive Director to steward its historic 640-acre site and to lead fundraising, partnerships, and public engagement. The role reports to the Board and works closely with the COO and senior staff to advance a shared mission of connecting people to the land and one another.

The successful candidate will drive strategic fundraising, oversee a diverse revenue mix including a market and events, and cultivate relationships with community partners and

Qualifications

• 10+ years in senior leadership of a complex organization.
• Extensive fundraising and philanthropic relationship building.
• Experience with budgeting and payroll responsibilities.
• Experience collaborating with boards in nonprofit governance.

Responsibilities

• Lead fundraising, cultivate major gifts and annual giving, and engage the Board as partners.
• Oversee sound financial management across programs and grow earned revenue from Market and events.
• Develop a strategic, fundable 10-year vision with the Board and staff.
• Act as the public face, building partnerships with local, state, and regional institutions.

Skills

Fundraising

Board relations

Budget management

Leadership

Job description

Job Opening: Executive Director

Brattleboro, Vermont – October 2026

Retreat Farm seeks an experienced, entrepreneurial, collaborative, and passionate executive to lead one of Vermont’s foremost champions of human and natural connection and community health. This is an opportunity to steward the historic farmstead and its 640 acres of forest, farmland, trails and waters and to fully activate these assets for the benefit of southeastern Vermont and beyond. Working with a dedicated staff and board and multiple community partners, the next Executive Director will lead the Farm into its second decade, working to build the foundation for a healthy community as we pursue our mission to connect people to the land and one another.

Organization Background

The nonprofit Retreat Farm, Ltd. was founded in 2015 to steward an expansive mid‑19th century farm, featuring nine historic barns, 11 miles of trails, and 640 acres of forests, organic croplands and accessible waters.

Adjacent to downtown Brattleboro, at the center of New England and a gateway to Vermont, Retreat Farm serves as a hub of community and natural connection. The Farm welcomes 100,000 visitors a year to its programs, events, market, trails and waters, offering four season access to learning, exploration, and connection.

At its core, Retreat Farm is devoted to the preservation, stewardship, and continuous improvement of The Farm Common – its forests, croplands, waters, trails, historic structures, and public spaces – and to making this expansive regional asset accessible and welcoming for the entire community. The Common provides an extraordinary platform for the Farm’s three centers of program activity.

• The Farmhouse Square activates Retreat Farm’s exceptional outdoor and indoor gathering spaces, recreation and learning opportunities to bring all members of the community together and strengthen its formal civil society as well.
• The Center for Food and Farming operates a local food market and cafe, leases 230 acres to organic farmers, and is developing additional resources in the 32,000sf former cheese factory – all in its effort to buoy local farmers and processors and help catalyze a healthy local food system.
• The Land and Its People utilizes an exceptional assembly of barns and adjacent pastures, gardens and forests as we build a comprehensive family‑oriented, educational and experiential resource, all rooted in the Farm’s natural and cultural history.

Our farmstead, trails and waters are open to everyone, every day. Each year we host 140 events and work with more than 50 partner organizations across the region. Our organic farm fields are in use by local and community farmers and our Farm Market showcases local food producers and makers. Our restored North Barn has become the most compelling and utilized indoor event space in the region and the go‑to gathering place for those working to advance the health of our community and the natural world.

Organization and Reporting:

The Executive Director reports to the Board of Directors and serves as the Farm’s principal external leader, responsible for fundraising, partnerships, public voice and board relations. The Executive Director works in close partnership with the Chief Operating Officer (COO), who leads internal operations.

The COO, Finance Director, and Managing Director of Development and Collaboration all report to the Executive Director. All other staff will report to relevant managers and ultimately the COO. Current staff is highly experienced and competent.

With the selection of the Executive Director, the founder of the organization will retire from the organization and board, but will continue to serve as a resource for fund‑raising and special projects related to the assessment of the impact of Retreat Farm, its food sources and community partners on the region’s health.

Principal Responsibilities

1. Lead fundraising. Personally cultivate and solicit major gifts, grow annual giving and membership. Complete the $10M endowment. Engage Board as fundraising partners.

2. Ensure financial strength. Oversee sound financial management across all programs, and grow earned revenue from the Market, private events and other business lines.

3. Lead the 10‑Year Vision. Turn the strategic vision into a considered, fundable plan, and work with the Board, staff and stakeholders to inform timing and sequenced.

4. Serve as public face and convener. Act as Retreat Farm’s spokesperson, build partnerships with local, state and regional institutions and agencies, and carry forward the Civil Discourse Series.

5. Activate the Food Center. Recruit and structure agreements with one or more tenants or partners to put the former cheese factory fully to work.

6. Partner with the Board. Support governance and planning with timely, transparent reporting, and help recruit and develop new board members.

7. Lead the team. Lead a staff of about 30 in close partnership with the Chief Operating Officer, building a culture of collaboration and accountability.

8. Steward the land and buildings. Ensure long‑term care of the Farm’s lands, historic buildings, trails and waters, with safe, welcoming public access.

Experience Required:

• 10 years or more as a senior leader of a complex organization or enterprise.
• Extensive fundraising, philanthropic relationship building, and/or complex sales experience.
• Deep interest in all or some of the following: rural economic development; local food systems; climate & environment; outdoor recreation; conservation & preservation; and civic engagement & civil society.
• Experience managing a budget, exhibiting fiscal accountability, and undertaking the responsibility to “make payroll.”
• Experience working with or for a Board of Directors and as a board member in nonprofit sector.

Preferred:

• Leadership of earned‑revenue operations such as retail, food, hospitality, venues or events.
• Experience negotiating leases, partnerships or other complex agreements.
• Working relationships with municipal and state government, agencies and organizations.
• Experience leading an organization through change or a leadership transition.
• Background in public programming, civic engagement, or arts and cultural partnerships.

Personal Attributes:

• Deep commitment to Retreat Farm’s mission and values.
• Ambitious, energetic and entrepreneurial mentality.
• Outgoing, collaborative, and partnership focus.
• Skilled and engaging communication, both written and spoken.
• Motivating leader with a team development orientation.
• Strong personal conviction and civic purpose in promoting Retreat Farm’s mission and vision.

Leadership Qualities:

• A disciplined builder: ambitious, but able to sequence growth carefully.
• A trusted, even-handed convener, comfortable bringing together people with differing views.
• A steward’s mindset: caring for a place that belongs to the community, and quick to share credit.
• High emotional intelligence, steadiness under pressure, and good humor.
• A visible, warm presence in the community, including at evening and weekend events.
• Interest in a long tenure to see the second‑decade plan through.

Compensation:

• $125-140,000 annual salary
• Employer contributions to Retreat Farm’s health, vision, and dental insurance plans
• Eligibility for enrollment in Retreat Farm’s SIMPLE IRA retirement savings plan with 3% employer matching
• A generous and flexible paid time off package
• Staff discount at the Retreat Farm Market

Start Date:

January 1, 2027 (target).

Retreat Farm, Ltd. is an equal opportunity employer and considers all candidates without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status or any other characteristic protected by law.