Office Manager/Executive Assistant, External Relations
  • Advancement

Dexter Southfield, Brookline, MA

Accredited by NEASC

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 team 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 a strong sense of initiative, this full-time Associate position may be your next career opportunity.

About You

You are a highly productive self-starter with excellent administrative, strategic, analytical, relationship-building, communications, and diplomacy skills. You are flexible and resilient, able to adapt to an ever-changing landscape, and pitch in whenever and wherever needed. Strong communication and interpersonal skills with a sharp attention to detail are your trademark. You have proven yourself as someone who can maintain an effective and well-organized office, and you tackle competing priorities with integrity, attention to detail, advanced organizational skills, and sound judgment.


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

  • Provide general administrative support for the Director of External Relations, Director of Marketing and Communications, and the Major Gifts Team.
  • Manages the Director of External Relations’ calendar, coordinating with the External Relations team and Dexter Southfield staff to schedule internal and external meetings.
  • Serves as constituent-facing contact for External Relations, exhibiting best practices in customer service and experience.
  • Serves as point person for handling all meeting coordination (scheduling, agenda, note taking, materials, food/room/location reservations, etc.) for: team meetings, committee meetings, donor visits, and other such large meetings.
  •  Manage the execution of key prospect stewardship efforts, including communications, gifts, events, etc.
  • Generate, coordinate, and track communications specific to major gift and/or special fundraising initiatives.
  • Prepare materials and briefings for capital solicitations, and work in concert with staff to complete follow-up with prospective donors.
  • Work with the Advancement Services Team to generate and execute queries, exports, and reports for Director / Major Gifts.
  • Track and process all department invoices and contracts.
  • Contribute to team planning and brainstorming sessions to generate ideas and recommend strategies.
  •  Learn new skills and technologies that drive toward successful results.
  •  Ability to effectively interact with colleagues, faculty, staff, administration, students, parents, and other community members
  •  Other duties as assigned.



  • Five or more years of work experience in an executive office environment.
  • Experience in the field of event planning a plus.
  • Familiarity with Raiser’s Edge or other development databases a plus.
  •  Bachelor’s degree

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 McCurdy Miller, Director of Development, at



  • Office Assistant