Major Gifts Officer
  • Advancement

Dexter Southfield, Brookline, MA

Accredited by NEASC

About Dexter Southfield

Dexter Southfield is an independent school where boys and girls in Pre-K through Class 12 develop their individual talents and build an ethical foundation for life. Through a classical education and innovative programming, students learn to lead with confidence and serve with compassion. Our 36-acre campus is located on the Brookline-Boston line, just miles from the city’s best museums, libraries, hospitals, colleges, and universities—all of which serve as an extension of our classrooms. At Dexter Southfield, we approach everything we do with enthusiasm and commitment, living by our School’s motto: “Our Best Today, Better Tomorrow.”


About Our Team

Our External Relations Office is made up of highly talented and professional team members who demonstrate exceptional commitment to customer service, excellence, and an unrelenting desire to surpass expectations. Their polish, expertise, and humility allow them to confidently collaborate with the Head of School, Board of Trustees, parents, alumni, volunteers, students, faculty, and peers. If you enjoy a fast-paced environment surrounded by positive teammates with an entrepreneurial spirit and strong sense of initiative, this full-time Major Gifts Officer position may be your next career opportunity.


About You

You are an experienced fundraising and relationship professional; a highly productive self-starter with excellent strategic, analytical, relationship-building, leadership, communications, and diplomacy skills. You are flexible and resilient, able to adapt to an ever-changing landscape, and help ensure that we craft and execute effective solicitation and stewardship strategies with strong internal coordination. This position requires a high level of skill in donor strategy development and requires a successful track record in relationship management. You are a strong verbal communicator and an excellent writer, with skill in development writing. You pitch in whenever and wherever needed. You have proven yourself as someone who can take on increased responsibility and you tackle competing priorities with integrity, humor, and sound judgment.  


To be successful in this role, you must be able to:

  • Develop and sustain excellent working relationships at all levels of the organization to generate interest and participation in stewardship initiatives.
  • Effectively represent Dexter Southfield to external audiences using strong verbal and written communication skills, especially in ways that enhance a person’s commitment to the organization.
  • Demonstrate solid stewardship experience: engage, inform, and interact with donors/prospects.
  • Display strong interpersonal and customer service skills: tact, self-confidence and assertiveness, diplomacy, teamwork, good judgment, confidentiality, a sense of humor, and excellent strategic planning skills.
  • Work independently, confidentially, and professionally interact with donors, families, and staff.
  • Manage and cultivate an individual portfolio of 100+ prospects (parents and alumni) rated as having capacity of $10,000 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
  • Identify and oversee prospect engagement meetings and follow-up with prospects in a timely and targeted manner
  • Work with the Director of Major Gifts to build strategic cultivation and stewardship plans, assist in writing donor appeals and funding proposals, and conceptualize donor cultivation/retention strategies for optimal outcomes
  • Work closely with the Director of Major Gifts, Director of Development, School administrators, volunteers, and faculty to identify and articulate gift opportunities and properly support them with accurate research and briefings when needed
  • Bring a strong understanding of current Advancement trends and a desire to develop professionally in the field of Advancement to the Dexter Southfield team
  • Actively contribute to External Relations Office planning and brainstorming sessions; generate ideas and recommend strategies for the betterment of processes, approaches, and new initiatives
  • Other duties as assigned



  • Four-year college degree required in related field; advanced degree highly desirable
  • At least 3-5 years of full-time development experience
  • Successful record of soliciting and closing gifts
  • Highly productive, self-starter with strong strategic, analytical, management, relationship building, communications, and diplomacy skill
  • Innate ability to think creatively and champion innovative concepts into action plans and proposals
  • Strong communication skills (orally, in writing, and editing)
  • Ability to establish and maintain effective working relationships with colleagues, parents, and other stakeholders
  • Sharp attention to detail
  • Strong analytical skills and well-developed business acumen
  • Natural relationship management instincts; savvy for gaining buy-in from various stakeholders
  • Working knowledge of fundraising database (Raiser’s Edge) to manage and track planned actions and accomplished moves with constituents
  • Commitment to excellence; willingness to go above and beyond
  • High energy and positive outlook; eagerness to take on an ambitious pace
  • Ability to plan, organize, develop, and conduct comprehensive promotions and initiatives
  • Ability to be flexible, effectively manage stress, and adapt to changing work priorities and assignments

At Dexter Southfield, we promote a culture of excellence that extends beyond academics, athletics, and the arts. We offer a community in which employees and students feel valued, respected, and a sense of belonging.


Interested candidates are encouraged to send a cover letter, resume, and completed employment application to Carmen Aliber, Director of Human Resources, at