Associate Headmaster

Trinity-Pawling School
Pawling, NY United States

Trinity-Pawling, one of the leading all-boys boarding schools in the country, is a close-knit community of over 100 employees and approximately 300 students. Our activities and efforts are focused on our mission which is to educate and instill a value system that prepares young men to be contributing members of society amidst the challenges of the ever-changing world.  Currently, we are seeking an Associate Headmaster to be the penultimate leader of the School responsible for the day-to-day student/faculty-based operations.

Essential Duties

  • Facilitates the school’s day-to-day academic operations by communicating directly with faculty, students, and/or parents regarding behavior, social, emotional, and/or academic issues and resolving issues to improve outcomes.
  • Working with the Headmaster, assumes significant oversight and responsibility for the day-to-day operations of the School.
  • Develops, implements, and supervises critical strategic goals for the School.
  • Assumes the leadership of the School in the absence of the Headmaster.
  • Develops, coordinates, and implements the annual school calendar, the school’s daily schedule, school duties assignments for all faculty and staff meetings, extracurricular activity schedules, and school-day special events.
  • Works in close partnership with the Headmaster to establish school priorities, particularly focused on academic programs, staffing, extracurricular, and parent involvement.
  • Foster a culture of student accountability by supporting the efforts of the Dean of Residential Life and Dean of Students, setting clear expectations, and ensuring faculty are skilled in conflict resolution and de-escalation strategies.
  • Build professional collaboration by advancing shared vision and goals as outlined by the Headmaster, discussing opportunities/challenges at regularly scheduled meetings, creating/utilizing cross-functional teams/committees; and encouraging the development of the professional learning communities.
  • Leads the accreditation process by reviewing and auditing standards, implementing corrective action as needed, and collaborating with senior leaders.
  • Serve as a collaborative leader in the School’s ongoing commitment to diversity, equity, and inclusion, in part by ensuring that programs/activities are inclusive, reflective, and supportive of the community.
  • Connect with students by residing on campus, engaging in extracurricular activities, and teaching one or more classes.
  • Promote the interest of students by being a good role model, establishing and reinforcing clear boundaries and guidelines, encouraging students’ autonomy and independence, and acting in a transparent manner.
  • Perform other duties as may be required.

Position Requirements

MS Degree in Education, Secondary School or a related field as well as experience in, and a strong understanding of Residence Life private school setting along with:

  • the ability to lead, support, and inspire employees
  • a personal and professional commitment to diversity, equity, and inclusion and the skills to facilitate critical conversations
  • a collaborative and relational style built on active solicitation of input, excellent listening skills, and a commitment to building consensus
  • a nuanced understanding of best practices in a boarding school
  • track record of delivering results

Must also possess:

  • prior experience in the development programs, systems, and strategic planning
  • academic leadership and the ability to mentor and manage performance
  • ability to formulate and articulate sound policies and as well as identify, resolve, and consult on a wide range of administrative and personnel issues with a clear sense of institutional needs and priorities
  • knowledge of mental health conditions and the ability to engage in emergency and crisis situations
  • a deep appreciation for the needs of adolescent boys
  • a strong respect for professional collegiality
  • willingness to adapt and maintain a positive orientation for change
  • ability to work weekends, evenings, and travel occasionally
  • a healthy sense of humor

Able to meet the physical demands, which include sitting for prolonged periods of time at a desk or computer workstation, using repetitive arm, hand and finger movements traveling on uneven terrain, climb/descend stairs, stand for long periods and carry up to 50 pounds.

Trinity-Pawling School complies with all applicable civil rights laws and does not discriminate based on any protected characteristics in any of its educational programs or activities, including employment. Protected characteristics (or protected classes) include race, color, religion, age, sex, sexual orientation, marital status, national origin, alienage, disability, pregnancy, veteran status, gender identity or expression, or any other basis prohibited by state or federal law. The School is specifically required by Title IX and other applicable federal and state laws not to discriminate in such a manner.

Contact Information


Interested parties should email a resume, a cover letter, and a statement of educational philosophy to Laurie DelBalzo, Director of Human Resources at