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
Email: hr@dextersouthfield.org
No phone calls please.​​


Job Openings:

Spanish I and II Teacher – Long-Term Substitute

Dexter Southfield seeks candidates for a maternity leave substitute teaching position for high school Spanish I and II, April 10-June 14, 2017. The position is open until filled. Candidates should complete the application found on the School’s website (http://www.dextersouthfield.org/userfiles/files/about/employment/Employment-Application.pdf) and send it with a cover letter and current resume to Stewart Tucker, Assistant Head of School, at stucker@dextersouthfield.org. 

Upper School Math Teacher

Dexter Southfield seeks candidates for an upper school (grades 9-12) math teaching position starting in the 2017-2018 academic year. In addition to teaching, the responsibilities include advising students and assisting with extracurricular activities. Helpful qualifications include experience in upper-level courses. Candidates should complete an application on the School’s website at http://www.dextersouthfield.org/userfiles/files/about/employment/Employment-Application.pdf and send it with a cover letter and current resume to Stewart Tucker, Assistant Head of School, at stucker@dextersouthfield.org.

Director of Parent and Alumni Relations

Job Summary:

Dexter Southfield School seeks a Director of Parent and Alumni Relations to involve and engage parents and alumni in the life of the School through programming, volunteer opportunities, special projects, and communications and to build awareness of and support for the School’s strategic plan and its first major capital campaign.

The Director will play a critical role in parent and alumni engagement, annual and capital fundraising, and stewardship efforts. Moreover, she/he will be a strategic partner to the Director of Advancement, the Board of Trustees, and the Head of School. The ideal candidate will possess an appreciation for independent schools and should have a demonstrated track record of success in building and strengthening relationships, generating excitement and support for an institution, increasing levels of responsibility, managing and maximizing volunteer efforts, building a team, and leading and working 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. 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, students, and faculty. Additionally, the Director must be a positive teammate and leader with an entrepreneurial spirit and strong sense of initiative. She/he must understand the importance of building relationships with current parents, both individually and collectively, at an independent day school so that this constituency may have an exceptional experience during their children’s time at Dexter Southfield. The School seeks someone with integrity, a sense of humor, and sound judgement. Finally, the Director 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:

  • Establish, grow, and oversee an official Dexter Southfield Parents Association.
  • Grow an early-stage alumni relations effort, implementing best practices
  • Develop, implement, execute, and evaluate annual parent engagement and alumni engagement plans
  • Recruit, train, support, and manage current parent and alumni engagement volunteers. Collaborate with the Director of the Dexter Southfield Fund on overall volunteer management efforts.
  • Create a vibrant five-year reunion program for classes celebrating 5th-50th reunions
  • Oversee and augment existing engagement efforts: Grandparents Day, Dexter Southfield Day, Coffee and Conversations, and other alumni events.
  • Create strategies for continued past family involvement with the School.
  • Manage the Alumni Board, comprised of 21+ alumni volunteers, whose purpose is to create greater connections between alumni and with the School.
  • With the Director of Major Gifts and Development Communications, develop and execute regular communications for parent and alumni audiences and implement social media and online communities to broaden parent and alumni engagement efforts.
  • Solicit and manage participation in Class Notes for the quarterly Alumni Magazine.
  • Solicit and manage a small portfolio of parent and alumni prospects.
  • Work closely with the Director of Advancement to develop and implement overall Advancement strategies, including preparing for, overseeing, and completing successful capital campaigns.


Qualifications and Personal Attributes:

  • Highly-productive, self-starter with strong strategic, analytical, management, relationship building, communications, and diplomacy skills
  • 7-10 years of relationship management, development and/or communications experience
  • Strong record of managing volunteers
  • Excellent management experience and proven track record of building strong teams
  • Strong attention to detail
  • Excellent project management, including proactive and independent development and implementation of work plans, timelines, and budgets
  • Strong analytical skills and well-developed business acumen
  • Natural relationship management instincts; savvy for gaining buy-in from various stakeholders
  • Innate ability to think creatively and champion innovative concepts into action plans and output
  • 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, please contact Peter G. Hamilton, Managing Director, Conley Search Group, by phone at 617.620.9268 or via email at peter@conleysearch.com

Contact Us

Phone: 617-522-5544

Email: info@dextersouthfield.org

20 Newton Street Brookline, Massachusetts 02445 Directions