Assistant/Associate Director of Parent & Alumni Relations (Advancement Office)
  • Advancement
  • Alumni Relations
  • Fundraising

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 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:

  • Work collaboratively with the Director of External Relations, the Director of Development, and other team members to develop and execute engagement strategies for parents and alumni.
  •  Support the Director of Development to execute strategy and initiatives determined in collaboration with the Parents Association Executive Committee and the Alumni Board; help manage Parents Association and Alumni Board volunteers.
  • Develop and execute strategy for several major on-campus events (Back to School events, Reunion, Dexter Southfield Day, Parents Association activities, alumni events, etc.):
    •  Lead weekly cross-campus collaboration meeting with Advancement, Admissions, Athletics & Operations
    • Serve as Advancement Office liaison to Operations, Food Services and Maintenance Teams
    • Prepare briefing materials for campus administrators and, for larger events, lead campus briefing meetings
    • Collaborate with Marketing & Communications team on event invitations
    • Engage and manage vendors
  • Collaborate with the Advancement Assistant to oversee additional event-related tasks, including:
    •  Producing nametags
    • Accurately preparing and tracking RSVP lists
    • Overseeing post-event data follow-up
    •  Managing event budgets, tracking receipts, check requests and invoices
    • Managing constituent data updates
  • Manage off-campus event logistics, relationships, and contracts
  • Oversee annual calendar of alumni and parent events and make recommendations on changes and additions to best serve the School and parent and alumni communities
  •  In collaboration with Marketing and Communications, oversee online alumni engagement platform, including the development and execution of a comprehensive alumni communications calendar
  • In collaboration with Marketing and Communications, oversee the development and execution of Parents Association and event communications. Recommend content for the Parents Association and event areas on the Dexter Southfield website.
  • Support the Director of Development and the Associate Director of the Dexter Southfield Fund with alumni annual giving strategies, including managing a small portfolio of alumni donors
  • Actively contribute to team planning and brainstorming sessions to generate ideas and recommend strategies  
  • Other duties, as assigned.


  •  5-7 years’ relevant experience or the equivalent combination of education and related or transferable work experience.
  • Bachelor’s degree
  • Demonstrated organizational and operational skills; superior interpersonal skills; excellent written and verbal communication; attention to detail.
  • Demonstrated ability to create, foster and work within an environment of collaboration.
  • Demonstrated high-level event planning and execution experience; project management experience.
  • Ability to synthesize and analyze data (primary and secondary sources) to turn information into effective strategies.
  • Ability to work independently and handle multiple priorities and deadlines simultaneously.
  • High degree of comfort with the use of technology, familiarity with Raiser’s Edge preferred.
  • High professional and ethical standards for handling confidential information.
  • Demonstrated initiative and resilience.
  • A team player with a positive, entrepreneurial, and service- and results-oriented attitude.
  • Ability to effectively interact with colleagues, faculty, staff, administration, students, parents, and other community members
  • Some evening and weekend work required.

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