THE MOUNTAIN SCHOOL OF MILTON ACADEMY 
151 Mountain School Rd. 
Vershire, VT 05079 

Director of Development 
Start Date: July 1, 2026 

The Mountain School of Milton Academy seeks a Director of Development beginning July 1, 2026. While the role is based on our campus in Vershire, Vermont, we are open to considering a hybrid work arrangement. 

The Mountain School is a semester-long, residential program for high school juniors set on 400 acres in central Vermont, where each fall and spring 45 students from across the country live and learn together. Through rigorous academics, hands-on work on a working farm, outdoor education, students develop independence, a strong sense of responsibility, and the value of a diverse community. 

Position Overview 

The Director of Development will lead all fundraising efforts at the Mountain School, reporting to, collaborating with, and advising the School Director. In this role, they will create and execute strategies for the Annual Fund, major gifts, and a multi-year fundraising plan that focuses on retaining donors, expanding the donor base, and increasing gifts. 

In addition, they will research and prepare grant applications and required stewardship reports for foundations and contribute development content to the school’s website, blog, and publications. 

Starting in their first year, the Director of Development will likely lead a major campaign for the Mountain School to fund critical strategic priorities. This includes: closing six figure gifts, supporting the School Director to close six and seven figure gifts, campaign event management, committee coordination, and more. 

The Director of Development will work in close partnership with outside consultants, who will provide campaign planning support, major gift coaching, prospect research and strategy, development operations guidance, grant writing services, and capacity-building resources. This partnership ensures the Director of Development has expert support throughout campaign execution while building sustainable internal development capacity. 

Committee & Community Leadership 

The Director of Development will provide leadership and staff support to the school's Alumni Committee, serving as the primary liaison between the committee and school leadership. This includes setting meeting agendas, coordinating committee activities, ensuring follow-through on initiatives, and leveraging committee members' networks for fundraising and engagement opportunities. 

During the campaign, the Director of Development will provide significant staff support to the Campaign Committee and campaign volunteer leadership. This includes: preparing meeting materials, coordinating volunteer solicitation activities, tracking campaign progress, managing volunteer assignments, and ensuring seamless communication between campaign leadership and school administration. 

Major Gifts & Operations 

The Director of Development will personally manage a portfolio of 50–75 major donor prospects and donors, with an annual revenue goal of $750,000–1 million from this portfolio. This includes conducting 100–120 meaningful donor interactions annually (visits, calls, cultivation events), personally making or participating in asks for five- and six-figure gifts, and advancing donors through strategic moves management. 

The Director will partner with the School Director on the top 15–20 relationships and will coach others on their donor engagement efforts. 

The Director of Development will have operational support for database management, gift processing, and donor communications. The Director of Development is responsible for ensuring these systems function effectively but will not personally execute all operational tasks. 

The Director of Development will collaborate closely with other administrators to ensure consistent messaging of the School’s narrative and to expand and enhance its visibility and reputation across social media, printed communications, and the website. Additionally, they will serve as a leader within the school community, actively participating in daily operations and engaging in hands-on involvement in the school’s activities. 

Essential Qualifications

• Personal track record of securing multiple six-figure gifts
• Experience leading or significantly participating in a campaign of $5M+
• Demonstrated ability to manage portfolio of 50+ major donors with revenue accountability 
• Experience coaching board members and volunteers in fundraising 
• Demonstrated leadership ability, with experience managing staff, volunteers, and/or boards in a mission-driven environment 
• Excellent interpersonal, communication, and presentation skills, with the ability to engage diverse stakeholders warmly and effectively 

Highly Desired Qualifications

• Independent school fundraising experience 
• Capital campaign experience 
• Experience with Raiser's Edge NXT specifically 
• Experience building development infrastructure from emerging to sophisticated 

Compensation & Benefits 

Compensation: Salary starts at $100,000 and increases for exceptional candidates with independent school capital campaign experience. Full-time positions include medical and dental insurance as well as a retirement plan. Other benefits include meals on campus from our “farm to table” kitchen, easy access to outdoor spaces and trails, and opportunities to pursue professional development. 

The Mountain School encourages candidates who would add to the racial, cultural, and gender diversity of the school community. 

Candidates will be required to complete criminal, sexual offender, and driving record check as well as fingerprinting checks. The Mountain School is an Equal Opportunity Employer. 

To Apply:

Interested and qualified candidates should submit electronically in one email and as separate documents (preferably PDFs) the following materials to Educator’s Ally
at leadershipsearch@educatorsally.com:

• A cover letter expressing interest in this particular position
• A current résumé
• List of references

Educator’s Ally provides senior leadership retained search services to independent schools throughout the U.S. With 50 years of experience working in support of independent K-12 school hiring, EA runs retained searches with the same personalized approach that has long distinguished out work in the contingency space, resulting in fluid and comprehensive processes and successful appointments.

Learn more at https://educatorsally.com/

About Educator's Ally

Educator's Ally connects teachers and administrators with independent day and boarding schools throughout the U.S. Since 1975, EA's highly personalized and thoughtful approach to recruiting has been valued by schools and candidates alike. We appreciate and understand each of our schools' unique characters and the importance of making the right match. Known for our commitment to establishing trusted relationships with both candidates and school administrators, EA carries out each of its searches with care and diligence. At no cost to our candidates, we offer support, guidance, and counsel throughout the search process. We know that job searches can be stressful and that teachers have busy schedules so partnering with EA is both smart and effective. We help candidates navigate the world of independent schools and connect them to opportunities that are the right fit.

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