Alliance for Catholic Education
Holy Trinity High School
Chicago, Illinois
Principal
Start Date: July 2026
holytrinity-hs.org
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.”
Mission
Holy Trinity's Mission is to challenge and nurture students academically, spiritually, and personally as they prepare for lives of leadership and service.
At a Glance
Established: 1910
Enrollment: 275
Total faculty: 24
Faculty with advanced degrees: 35%
Faculty of color: 35%
Students of color: 92%
Student/teacher ratio: 12:1
Financial aid budget: $583,000
Annual giving: $2.4 million (significantly supported by Board of Trustees)
Students receiving aid: 93%
AP and Honors courses: 26
Sports teams: 12
Student clubs: 32
Endowment: $4.8 million
Annual operating budget: $5.2 million
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.
To Apply
Interested and qualified candidates are invited to contact the consultants in confidence regarding this position. Per the compensation notice requirement of Illinois (HB) 3129, the compensation range is $100K -$130K. Candidates ultimately will need to submit the following materials as separate PDF documents to the consultants:
• A cover letter expressing their interest in this particular position;
• A current résumé;
• A completed Candidate Questionnaire (to be provided by consultants);
• A list of five professional references with name, relationship, phone number, and email address of each (references will not be contacted without the candidate’s permission) to:
Michael R. “Mike” Truesdell
Senior Consultant
michael.truesdell@carneysandoe.com
Tom Lengel
Senior Consultant
tom.lengel@carneysandoe.com