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Dexter Southfield School offers boys and girls from Pre-Kindergarten through Class 12 a classical education. Our 36-acre campus is located in South Brookline on the Boston-Brookline line, with easy access to Boston. Dexter Southfield offers a collaborative, community atmosphere and excellent benefits.

Dexter Southfield seeks to attract faculty and staff who will uphold the work and values of the School in order to strengthen the community of students, parents, faculty, and staff. Successful candidates will have a commitment to being in and supporting a community which focuses on the education and well-being of students in a variety of settings both in and outside the classroom.

The School considers applicants without regard to race, color, religion, sex, age, disability, sexual orientation, familial or marital status, or any other characteristics protected from discrimination under state of federal laws.

Interested candidates should download the printable PDF employment application and submit this completed application, along with a cover letter, a resume and salary requirements, to:
Human Resources
Dexter Southfield
20 Newton Street
Brookline, MA 02445-7498
No phone calls please.​​


Job Openings:

Major Gift Officer

The Opportunity

Dexter Southfield School seeks a Major Gift Officer to fundraise in support of the School’s strategic plan and its first major capital campaign.

The Major Gift Officer will play a critical role in parent and alumni engagement, annual and capital fundraising efforts, and stewardship. The ideal candidate will possess an appreciation for independent schools and should have a demonstrated track record of success in annual and major gift fundraising, identifying and stewarding top prospects, and working collaboratively with others. Willingness to participate with enthusiasm in the full life of an independent school community is essential.

The Candidate

The successful candidate will demonstrate a commitment to customer service, professionalism, leadership, and excellence and have strong knowledge of industry best practices and procedures. She/he will exhibit a mix of intelligence, sophistication, and humility so that she/he may confidently collaborate with the Advancement team, the Head of School, the Board of Trustees, parents, alumni, volunteers, students, and faculty. Additionally, the Major Gift Officer must be a positive teammate and leader with an entrepreneurial spirit and strong sense of initiative. The School seeks someone with integrity, a sense of humor, and sound judgement. Finally, the Major Gift Officer will be someone who approaches her/his work with cheerful persistence and lives by the School’s motto: “Our Best Today, Better Tomorrow.”

Primary Responsibilities:

  • Manage and cultivate an individual portfolio of 100+ prospects (current and past parents, alumni) rated as having capacity of $50,000 and above, as well as solicit annual fund gifts as needed / appropriate with prospects
  • Meet and exceed revenue and outreach goals by directly soliciting gifts and overseeing all facets of the fundraising process including prospect identification, cultivation, closing and stewarding of prospects
  • Solicit planned gifts on behalf of the School; identifying key planned giving prospects and demonstrating the knowledge and strategic skills to successfully close planned gifts
  • Work closely with the Director of Major Gifts, Director of Advancement, School administrators, volunteers and faculty to identify and articulate gift opportunities and properly support them with accurate research and briefings when needed
  • Identify and oversee prospect engagement activities/events and follow-up with prospects from events in a timely and targeted manner
  • Write personalized, timely, and thoughtful communications to prospects after properly researching and tailoring messages based on donor type, capacity, background, etc.  These include letters, emails, invitations, and proposals.
  • Bring a strong understanding of current Advancement trends and a desire to develop professionally in the field of Advancement to the Dexter Southfield team


Qualifications and Personal Attributes:

  • Highly-productive, self-starter with strong strategic, analytical, management, relationship building, communications, and diplomacy skills
  • 8-10 years of development experience
  • Successful record of soliciting and closing gifts
  • Strong writing and editing skills with a sharp attention to detail
  • Strong analytical skills and well-developed business acumen
  • Natural relationship management instincts; savvy for gaining buy-in from various stakeholders
  • Commitment to excellence; willingness to go above and beyond
  • High energy and positive outlook; eagerness to take on an ambitious pace


Salary is competitive and will be commensurate with experience

Interested candidates should send a cover letter and resume to Casey Hassenstein, Director of Major Gifts and Development Communications, at

Contact Us

Phone: 617-522-5544 • Absence Reporting Line: 617-751-3400


20 Newton Street Brookline, Massachusetts 02445 Directions