Career Opportunities

Holy Trinity High School is committed to hiring exceptional faculty and staff who have a passion for excellence and a commitment to serving. Explore the current openings.

Why Join the Holy Trinity Community?
At Holy Trinity High School, we are small by design—with fewer than 300 students, you’ll truly know every name and face in our building. We champion a collaborative culture that respects your expertise, providing protected time for peer work and the unique perk of early dismissal every Thursday. Our community thrives on shared purpose, whether we’re giving back during our whole-school service days or bonding during our annual retreats. If you’re looking for a close-knit environment where your impact is visible and your growth is supported, you belong at Holy Trinity.

Our Mission
Holy Trinity High School, a school in the Holy Cross tradition, challenges and nurtures students academically, spiritually, and personally as they prepare to lead lives of leadership and service. Every teacher at Holy Trinity understands, accepts, and articulates this mission while providing a program of supervision, instruction, and evaluation for the students in their care.

Principal

Overview
Holy Trinity High School in Chicago seeks a dynamic and visionary Principal for July 1, 2026. Founded by the Brothers of Holy Cross in 1910, Holy Trinity is the second oldest high school ministry of the Congregation of Holy Cross in the United States. With the guidance of the Brothers, Holy Trinity High School is committed to educating the whole person, fostering a love of learning, and providing a rigorous learning experience. Holy Trinity High School is a highly supportive and distinguished Catholic, coed, grades 9-12, preparatory institution serving a diverse and inclusive community.

The school, considered a “hidden gem” among Chicago Catholic schools, is known for its unique focus on students, family, and community. With an active and caring Board of Trustees and strong leadership from its new President Elizabeth Torres, Holy Trinity has been able to attract impactful philanthropic support which has helped the school recently complete an $8.1 million capital campaign. Additionally, the School raises well over $1 million from The Guardians of Hope Gala, an annual community event of remarkable success. Known for having a devoted and dedicated faculty and staff, Holy Trinity has a rich tradition of academic excellence and a mission deeply rooted in helping students achieve an education that is not simply measured by the grade they earn, but by the quality of their character and their commitment to social justice.

Holy Trinity High School seeks to foster a love of learning among its students and has consistently evolved to meet the challenges of the 21st century. The School’s commitment to a holistic approach to education is reflected in its Belief Message stemming from a thorough marketing and branding study: “At Holy Trinity, we know great education starts with what you learn — and becomes more powerful when it shapes who you are. Every day, we support and inspire one another to pursue new challenges, growth, and deeper meaning. When students focus on their purpose, they develop the determination to change their world.”

Opportunities and Challenges
Holy Trinity seeks a Principal who is spiritually grounded, academically astute, and relationally gifted. The next Principal should understand the opportunities and challenges of serving as a Leader of a school comprised largely of first generation private school students and families.

Major responsibilities for the next Principal include:
• Overseeing and promoting high standards and expectations for all students;
• Articulating a clear academic vision that is communicated fully both internally and externally;
• Balancing enrollment growth with admissions standards;
• Maintaining and supporting diversity;
• Recruiting, supporting, and developing well qualified teachers via a comprehensive faculty development program so that teachers can grow and thrive as members of the Holy Trinity community:
• Ensuring the School is operating in an academic environment of best practices.

Qualifications and Personal Attributes
The ideal candidate will possess the following qualities and qualifications:
• A mission-driven leader who can fully appreciate and articulate the values of a Holy Cross sponsored, Catholic, faith-based education;
• A graduate degree, preferably in educational leadership or curriculum;
• Knowledge of and interest in securing and/or implementing funding from state and federal education resources, ie Title I and similar funding;
• Proven leadership experience, with demonstrated success in academic program development, faculty engagement, and community building;
• An excellent communicator with exceptional written and oral communication skills, capable of articulating the school’s mission with clarity and inspiration to diverse audiences;
• Teacher at heart who genuinely enjoys working with young people and understands the classroom experience from a place of personal practice and passion;
• Visible and relational presence, able to be actively engaged in the life of the School;
• Strong cultural competency, capable of leading a diverse school community with grace, humility, and conviction;
• Experienced teacher and knowledgeable professional resource able to provide observation, evaluation support and conversation to both new and veteran teachers;
• Enthusiasm to lead in partnership with a team of invested and experienced colleagues, and an appreciation for the School’s well-established history and traditions.

Religion Teacher

Core Instructional Responsibilities
1. Academic Challenge (The Mind)
● Curriculum Excellence: Plan and implement a rigorous theology curriculum congruent with departmental and school guidelines.
● Critical Thinking: Foster intellectual curiosity by helping students connect “ancient truths” to contemporary life and ethical issues.
● Inclusive Instruction: Utilize diverse instructional strategies to ensure all learners are challenged and supported, providing specific academic tutoring for students at risk of failure.
● Growth & Research: Keep abreast of new developments in educational research and the theological field through conferences, journals, and workshops.

2. Spiritual & Personal Nurturing (The Heart)
● Holy Cross Identity: Integrate the Holy Cross charism (e.g., Spes Unica—the Cross as our only hope) into classroom culture, reflections, and daily interactions.
● Safe Exploration: Create a classroom environment where students feel safe to explore their relationship with God and their personal faith journey.
● Liturgical Life: Collaborate with the Religion Department and Campus Ministry to contribute to the liturgical life of the school and participate in at least one student retreat per academic year.

3. Preparation for Leadership & Service
● Social Justice: Incorporate Catholic Social Teaching as a framework for leadership
● Theological Reflection: Mentor student-led service projects, ensuring they are rooted in deep theological reflection rather than simple volunteerism.

Professional & Supervisory Duties
1. Student Supervision & Safety
● Assigned Supervision: Participate in Advisory program and perform duties such as cafeteria supervision, study group or tutoring session monitoring, and supervision of assigned student areas for community period or other school events.
● Substitution: Accept substitution duties for peers when needed to ensure continuity of student care.

2. Community Engagement & Administration
● Communication: Maintain regular contact with parents, guardians, and sponsors regarding student progress.
● Record Keeping: Maintain accurate attendance records for all teaching and supervisory periods.
● Policy Adherence: Uphold all school policies as outlined in the Student Agenda and Employee Handbook.
● Departmental Support: Participate in the school improvement process and attend all faculty and departmental meetings.

Institutional Participation & Requirements
1. Mandatory Events & Extracurriculars
● School Calendar: Participate in key school events Parent Meetings, Back-to-School
Night, Parent-Teacher Conferences, Open Houses, Ninth Grade Entrance/Registration
days, Senior Robing, Honors Programs, and Graduation.
● Event Supervision: Supervise at athletic events and one social event (prom, dance, etc)
per semester.

Biology & General Science Teacher

Core Instructional Responsibilities:
1. Academic Challenge (The Mind)
● Instruction: Plan and implement a rigorous Science curriculum aligned to skills and standards to prepare students for college
● Scientific Inquiry: Foster critical thinking and intellectual curiosity by guiding students through the scientific method, data analysis, and evidence-based reasoning.
● Inclusive Instruction: Utilize diverse instructional strategies and laboratory experiences to ensure all learners are challenged. Provide specific academic tutoring for students at risk of failure.
● Lab Management: Maintain a safe, organized, and well-equipped laboratory environment, ensuring all experiments adhere to safety protocols and ethical standards.
● Professional Growth: Keep abreast of new developments in STEM education and  scientific research through conferences, journals, and workshops.

2. Spiritual & Personal Nurturing (The Heart)
● Stewardship of Creation: Integrate the Holy Cross charism into culture of the classroom
● Participate in school masses, prayer services, and other school-wide faith formation events

Professional & Supervisory Duties
1. Student Supervision & Safety
● Assigned Supervision: Participate in Advisory program and perform duties such as
cafeteria supervision, study group or tutoring session monitoring, and supervision of
assigned student areas for community period or other school events.
● Substitution: Accept substitution duties for peers when needed to ensure continuity of
student care.

2. Community Engagement & Administration
● Communication: Maintain regular contact with parents, guardians, and sponsors regarding student progress.
● Record Keeping: Maintain accurate attendance records for all teaching and supervisory periods.
● Policy Adherence: Uphold all school policies as outlined in the Student Agenda and Employee Handbook.
● Departmental Support: Participate in the school improvement process and attend all faculty and departmental meetings.

Institutional Participation & Requirements
1. Events & Extracurriculars
● School Calendar: Attend Fall Parent Meetings, Back-to-School Night, Parent-Teacher Conferences, Open Houses, Ninth Grade Entrance/Registration days, and Graduation.
● After-School Involvement: Lead or organize after-school activities or clubs (e.g., Pet Club, Science Olympiad, Robotics, or Sustainability Club).
● Event Supervision: Supervise athletic events and one social event per semester.

Long-term Permanent Substitute Teacher

This position for the rest of the 2025-2026 school year. The first 3 months will be as a substitute for a math teacher on leave, after that as a default substitute in any class. The candidate must understand the content and be able to explain, present, and support students with the high school math curriculum. Candidates must create and manage the classroom in a positive manner, respecting the dignity of all. Each Teacher/Employee understands,  accepts, and articulates the Mission Statement of Holy Trinity High School and provides for a program of supervision, instruction, and evaluation of students charged to his/her care. 

Duties and Responsibilities

• Teaches a schedule of classes and performs other assigned duties as determined by the School such as: 
  • conduct an advisory program 
  • supervise the cafeteria
  • supervise study groups 
  • be available for student tutorial assistance and consultation 
  • accept substitution coverage for other classes duty when needed
  • supervise assigned student workers
• Gets involved in leading and organizing after school activities/clubs.
• Maintains accurate attendance records for all teaching and supervisory periods.
• Supervises hallways and common areas during all passing periods and at dismissal.
• Communicates on a regular basis with parents/guardians and sponsors regarding their students’ progress.
• Keeps abreast of new developments in educational research and teaching field through conferences, journals, workshops, etc.
• Attends and participates in all faculty meetings.
• Fully participates in the school improvement process (SIP).
• Provides supervision at extracurricular events as needed.  All Faculty and Staff must supervise at least three athletic events per year and one social event per semester.
• Provides for academic tutoring for students at risk of failure.
• Provides for a safe and controlled environment conducive to the learning process.
• Upholds all policies as outlined in the Student Handbook and Employee Handbook. 
• Attends and participates at one of the student retreats during the academic year.
• Plans and implements lessons congruent to curriculum guidelines.
• Attends Fall Parent Meetings, Back-to-School Night, Parent-Teacher Conferences, Open Houses, one Ninth Grade Entrance Test day and one of the Ninth Grade Registration days, the Senior Robing, Honors Programs, and Graduation, and other mandatory events.
• Agrees to support the Guardians of Hope major fundraising event by either attending the event and/or by helping with the preparation for or clean up from the event.
• Maintains or works toward completing certification as required.
• Fulfills other tasks as assigned by the Administration
• Comply with the Archdiocese of Chicago Protecting God’s Children Requirements (Background Screening, Fingerprinting, VIRTUS Training, CANTS, Code of Conduct)

Job Type: Full-time
Pay: $40,000 – $50,000 depending on experience level.
Benefits: Medical, Dental and Vision, 403b, Life, Short-Term and Long-term Disability insurance.

Non-Discrimination Policy

Holy Trinity High School will not engage in discrimination or harassment against any person because of race, color, religion, sex, national origin, ancestry, age, order of protection status, genetic information, marital status, disability, sexual orientation including gender identity, unfavorable discharge from the military or status as a protected veteran and will comply with all federal and state nondiscrimination, equal opportunity and affirmative action laws, orders, and regulations. This nondiscrimination policy applies to student admissions and employment.

We invite you to become a part of our community and Holy Trinity High School makes a deliberate effort to employ faculty and staff of diverse races, ethnicities, and backgrounds. 

Resumes can be sent to humanresources@holytrinity-hs.org. No phone calls please.