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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
No phone calls please.​​


Job Openings:

Development Associate

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 Advancement 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 Advancement 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 writing and editing skills with a sharp attention to detail are your trademark. You have a 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:

·         Provide administrative support to the Major Gift Team and other teams, as needed.

·         Coordinate information tracking, collection, and entry.

·         Generate and execute queries, exports, and reports.

·         Create, plan, and implement donor and prospect events.

·         Manage individual and team output, tracking progress toward goals.

·         Oversee special projects related to stewardship/recognition/prospect engagement efforts

·         Create and implement project management plans to execute initiatives.

·         In concert with the Director of Major Gifts and Development Communications, generate, coordinate, and track communications specific to major gift and/or special fundraising initiatives.

·         Actively contribute to team planning and brainstorming sessions to generate ideas and recommend strategies

·         Conduct prospect research and analysis of confidential donor information; provide information to colleagues, institutional leadership, and other constituents.

·         Plan donor visits, reach out to alumni and parents as needed, prepare briefings,  and complete follow-ups.

·       Attend committee meetings; generate and distribute minutes.

·         Manage and coordinate the advancement communications and events calendar.

·         Learn new skills and technologies that drive toward successful results

·         Other duties as assigned.


·         Five or more years of work experience in an office environment

·         Working knowledge of Raiser’s Edge database highly desirable

·         College degree preferred


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 Urbonas, Director of Human Resources, at

Director of College Counseling

Dexter Southfield ( is an independent day school founded in 1926 with 840 students in PreK through Class 12, a faculty and staff of 190, and 70 seniors each year. The school’s well-resourced 36-acre campus is located on the Brookline-Boston line, just 5 miles from the center of Boston and close to some of the world’s best museums, libraries, hospitals, colleges, and universities—all of which serve as an extension of the school’s classrooms. Dexter Southfield seeks a strong, outcome-oriented Director of College Counseling to lead its college counseling program, starting in July 2018.

Dexter Southfield’s core academic and co-curricular programs are enhanced by signature features including leadership and public speaking in all divisions, a research-grade astronomical observatory, and connections with the Museum of Fine Arts, Harvard University, and Angell Memorial Hospital, which represent the school’s commitment to using the “city as a campus.” Approaching everything with enthusiasm and commitment, students take advantage of opportunities both on campus and around the metropolitan area to build experiences that prepare them well for the most selective colleges and universities. The coed 280-student Upper School (Classes 9-12) builds on the foundations of the single-sex Lower (Pre-K through Class 5) and Middle (Classes 6-8) Schools.


The school “helps boys and girls develop their individual talents and build an ethical foundation for life” so that “students learn to lead with confidence and serve with compassion, living by the motto, ‘Our Best Today, Better Tomorrow.’”

The Position & Responsibilities

Dexter Southfield is committed to a college counseling program that focuses on the individual student’s goals and interests and helps each student find the best set of post-secondary outcomes. The school is eager for a Director of College Counseling who will proactively and enthusiastically represent Dexter Southfield and its students to colleges and universities.

Dexter Southfield’s next Director of College Counseling will report to the Assistant Head of School and will manage an office of highly engaged professionals including the Associate Director of College Counseling and the College Office Manager. The office also has administrative support on a part-time basis from the Registrar. The Director collaborates frequently with the Head of the Upper School and on an ad hoc basis with the Director of Athletics, the Director of Admissions and Enrollment Management, and the Director of Communications. The Director of College Counseling reports periodically to the Board of Trustees.

The Director’s primary responsibility is to lead a proactive, intentional college counseling program that will ensure each student generates the best set of post-secondary outcomes possible. To that end, responsibilities include the following:

  • Developing and implementing a multi-grade program of education and support beginning with the ninth grade to ensure students and their parents understand the college process and how decisions and choices throughout the secondary school years can impact the college process
  • Initiating and maintaining strong relationships with colleges on behalf of the school, hosting college admissions visitors, visiting a range of campuses, and communicating directly with college officials on behalf of students
  • Ensuring that the College Office is highly-organized with efficient systems, policies, and communication protocols that enable the efficient management of standardized testing and student applications
  • Educating students, parents, prospective families, faculty and board members about all aspects of the college process including standardized testing, athletic recruitment, scholarships, financial aid, and the current college admissions landscape
  • Working closely with other leaders in the school to ensure that the school’s academic and other programs position graduates for success in the college search and application process as well as in college
  • Analyzing data and communicating trends and projections around which new initiatives and strategies will be designed
  • Serving as an active college counselor to approximately half of each class
  • Regularly pursuing opportunities for professional growth, including relevant conferences with plane travel and overnight stays, and networking within the industry
  • Ensuring continued professional growth of the personnel in the college office



Dexter Southfield seeks an individual with strong communication, presentation, and leadership skills with deep knowledge of, and proven experience in, the college admissions process to serve as its Director of College Counseling. Individuals who have gained at least 10 years’ experience as a college counselor in competitive independent schools or as an officer in highly selective college admissions will be of particular interest. A bachelor’s degree is required, and an advanced degree is preferred.

The Director of College Counseling embraces the school’s mission and culture and:

  • Has the leadership skills to serve enthusiastically as the visible, vocal, and strategic leader of the school’s college counseling program
  • Is a highly organized professional who thrives in a fast-paced environment
  • Enjoys and cultivates personal interactions with students, parents, faculty and college representatives
  • Has strong communication skills as a speaker, writer, and listener
  • Demonstrates patience and support in working with students and parents
  • Serves as an enthusiastic and highly knowledgeable ambassador for the school and its students in the college process, dividing 25 campus visits annually with the Associate Director and building relationships with college admissions professionals
  • Demonstates strong presentation and communication skills to a diverse audiences, including students, parents, faculty, trustees, prospective families, other college counselors, and college representatives
  • Has a proven track record as a successful team leader and team builder
  • Is an active, visible member of the school community, attending student events such as games, theater productions, and assemblies  
  • Has strong and demonstrable successful experience in the field
  • Demonstrates proficiency with college counseling software such as Naviance
  • Is committed to professional growth
  • Has a sense of humor


This is an opportunity to be part of a strong, positive school community. A visit to the school will quickly reveal that Dexter Southfield is a place people genuinely like to be each day; it is a school marked by good collegiality and humor. Members of the school community agree that there is not a “typical” Dexter Southfield student, although “positive, respectful and very polite” are common denominators as well as an achievement orientation and “interest in things outside themselves.”

The new Director of College Counseling will have the opportunity to take a leadership role to define and promote a unified vision and message regarding the college counseling program that can be well-articulated consistently throughout the school. This is a wonderful opportunity for a strategic and goal-oriented college counseling professional to join a great school community and work with a strong team to build on the numerous strengths of the current college counseling program.


For Consideration

Interested individuals should submit a current resume and a letter of interest to:

Jane Armstrong or Bill Lyons, Managing Partners    

Independent Thinking



Dexter Southfield 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 or federal laws.

Major Gift Officer

The Opportunity

Dexter Southfield School seeks a Major Gift Officer to fundraise in support of the School’s strategic plan and its first major capital campaign.

The Major Gift Officer will play a critical role in parent and alumni engagement, annual and capital fundraising efforts, and stewardship. The ideal candidate will possess an appreciation for independent schools and should have a demonstrated track record of success in annual and major gift fundraising, identifying and stewarding top prospects, and working collaboratively 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 and have strong knowledge of industry best practices and procedures. 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, volunteers, students, and faculty. Additionally, the Major Gift Officer must be a positive teammate and leader with an entrepreneurial spirit and strong sense of initiative. The School seeks someone with integrity, a sense of humor, and sound judgement. Finally, the Major Gift Officer 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:

  • Manage and cultivate an individual portfolio of 100+ prospects (current and past parents, alumni) rated as having capacity of $50,000 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
  • Solicit planned gifts on behalf of the School; identifying key planned giving prospects and demonstrating the knowledge and strategic skills to successfully close planned gifts
  • Work closely with the Director of Major Gifts, Director of Advancement, School administrators, volunteers and faculty to identify and articulate gift opportunities and properly support them with accurate research and briefings when needed
  • Identify and oversee prospect engagement activities/events and follow-up with prospects from events in a timely and targeted manner
  • Write personalized, timely, and thoughtful communications to prospects after properly researching and tailoring messages based on donor type, capacity, background, etc.  These include letters, emails, invitations, and proposals.
  • Bring a strong understanding of current Advancement trends and a desire to develop professionally in the field of Advancement to the Dexter Southfield team


Qualifications and Personal Attributes:

  • Highly-productive, self-starter with strong strategic, analytical, management, relationship building, communications, and diplomacy skills
  • 8-10 years of development experience
  • Successful record of soliciting and closing gifts
  • Strong writing and editing skills with a sharp attention to detail
  • Strong analytical skills and well-developed business acumen
  • Natural relationship management instincts; savvy for gaining buy-in from various stakeholders
  • 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 should send a cover letter and resume to Casey Hassenstein, Director of Major Gifts and Development Communications, at

Contact Us

Phone: 617-522-5544 • Absence Reporting Line: 617-751-3400


20 Newton Street Brookline, Massachusetts 02445 Directions