Assistant Director of the Dexter Southfield Fund

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 may be your next career opportunity. 

About You

You are an experienced development professional with entrepreneurial and strategic vision who is looking to actively lead and contribute to efforts to build a culture of philanthropy at Dexter Southfield. You are constructive, positive, action-oriented, and have the desire to work within a dynamic, face-paced, and goal-centered institution. You have effective interpersonal skills and are highly capable of working with, building trust, and earning the respect of the Head of School, Board of Trustees, Admissions and Marketing and Communications colleagues, as well as the faculty, students, and other staff of Dexter Southfield.

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

  • Develop the strategic direction and implementation of the Dexter Southfield Fund.
  • Create and execute strategies to meet Fund goals from all constituencies, including current and past trustees, parents, alumni, grandparents, faculty and staff, and friends.
  • Create a year-long marketing plan that includes innovative messaging to communicate the importance of the Dexter Southfield Fund, and to create enthusiasm and engagement throughout the year in the effort.
  • Manage the production of direct mail and email appeals, and other print and digital collateral to build awareness for the Fund.
  • Recruit, train, and manage parent volunteer solicitor team. Serve as the main point of contact for the team, including the Fund co-chairs.
  • Lead the Senior Parent Gift and Senior Class Gift efforts.
  • Create and oversee meaningful engagement and recognition events and activities to increase giving and appreciation among donors and volunteers.
  • Build relationships with Dexter Southfield parents, alumni, faculty, and staff.
  • Serve as a valuable contributor to the Advancement team, taking on and helping with additional projects as necessary, sharing knowledge and best practices, and continuing to learn.
  • Actively contribute to Advancement Team planning and brainstorming sessions; generate ideas and recommend strategies for the betterment of processes, approaches, and new initiatives.
  • Other duties as assigned


  • Bachelor’s degree and a minimum of 3-5 years of full-time work experience in the development field, preferably at an independent school.
  • Proven track record of fundraising success by meeting organizational goals and initiating and implementing ideas to achieve results.
  • Proficiency with knowledge of Raiser’s Edge fundraising software and/or the ability to master use of the system within three months.
  • Ability to develop and implement successful strategies and pivot around obstacles to achieve results.
  • You have proven yourself as an effective team player who can be counted on to address needs and identify and implement creative solutions.
  • You are confident and poised and committed to fulfilling the School’s motto “Our Best Today, Better Tomorrow.”
  • Team player with strong communication skills (written, oral, non-verbal) and a detail-oriented mindset.
  • Ability to be flexible, effectively manage stress, and adapt to changing work priorities and assignments.
  • Ability to work both independently and as part of a team to establish and nurture effective working relationships with students, faculty, staff, and parents.
  • A good sense of humor.

At Dexter Southfield, we promote a culture of excellence that extends beyond academics, athletics, and the arts. We offer a culture in which employees feel valued and respected and are rewarded with a generous employee benefit package. 

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