Assistant Headmaster

Assistant Headmaster

Divine Mercy Academy
Pasadena, Maryland

About Divine Mercy Academy

Divine Mercy Academy is a classical K-8 school that utilizes the Catholic Liberal Education model to create Saints and Scholars. Our purpose is to know, love, and serve God and to form others so they might joyfully do the same. Divine Mercy Academy provides students with a foundation by which they are truly made free to seek truth and live joyful, productive lives informed by reason and virtue in order to help bear witness to the kingdom of God in our day.

Position Overview

The Assistant Headmaster serves as a senior leader responsible for student life, discipline, and the daily functioning of Divine Mercy Academy. Working in close partnership with the Headmaster, this role ensures that school policies, expectations, and procedures are implemented consistently and faithfully.

 

Primary Responsibilities

Student Life & Discipline

The Assistant Headmaster holds primary responsibility for the day-to-day administration of student discipline.

• Oversee daily student conduct and behavioral matters
• Respond to incidents and manage follow-up in accordance with school philosophy
• Assign and oversee appropriate disciplinary consequences
• Maintain discipline documentation and records
• Track behavioral patterns and identify emerging concerns
• Escalate serious or complex matters to the Headmaster
• Recommend major disciplinary actions for Headmaster approval
• Ensure consistent enforcement of expectations across grades and tutors

Attendance & Punctuality

• Monitor daily attendance and tardiness
• Track patterns of chronic absence or lateness
• Coordinate interventions with families as needed
• Report attendance trends and concerns to the Headmaster

Policy Review & Implementation

• Review school policies and procedures on a regular basis
• Identify inconsistencies, gaps, or areas in need of clarification
• Recommend revisions to the Headmaster
• Ensure day-to-day practices align with approved policies
• Support staff understanding and adherence to procedures as directed

Daily Operations & School Functioning

• Support the smooth functioning of the daily school schedule
• Address operational disruptions as they arise
• Assist with logistics for testing days and special events
• Serve as point person for student life matters during the school day
• Coordinate emergency response procedures in consultation with the Headmaster

Teaching Responsibilities

• Teach one course, assigned annually in consultation with the Headmaster
• Participate fully in faculty life and meetings
• Model professionalism, consistency, and adherence to school expectations

Role Growth & Discernment

Divine Mercy Academy has never previously held the position of Assistant Headmaster. As such, this role is intentionally designed with flexibility and discernment in mind. Responsibilities may evolve over time based on the needs of the school and the strengths of the individual, particularly as Divine Mercy Academy grows toward a full K–12 program. The Assistant Headmaster should be eager to grow with the school and be open to an evolving scope of leadership.

As Divine Mercy Academy prepares to grow into a full K–12 program by Fall 2027, the roles and responsibilities may adapt and adjust as needed for a growing school. Such developments will be determined in mutual consultation with the Headmaster as determined by the match of charism, gifts, and talents.

 

Ideal Candidate

The ideal candidate for Assistant Headmaster at Divine Mercy Academy will demonstrate:

• A clear love for Jesus Christ and a desire to serve His Church
• A strong understanding of classical education and the Catholic Liberal Arts tradition
• A desire to be a lifelong learner
• A strong desire to partner with parents as the primary educators of their children
• Alignment with the mission and vision of Divine Mercy Academy
• Excellent written and verbal communication skills
• Sound judgment, presence, and confidence in working with students and families
• Flexibility and adaptability in a growing school environment
• A strong work ethic and a willingness to take initiative
• Prior experience in school administration or leadership
• A graduate degree in Education, School Leadership, or a related field
• Experience in a Catholic classical school is strongly preferred

Application Process

Interested candidates should submit a resume, cover letter, and two professional references to Jacqueline Dolch at administrator@divinemercy.md.