Holy Trinity High School | Principal

Overview

Holy Trinity High School
Chicago, Illinois
Principal

Start Date:

July 2026
Holy Trinity-hs.org

Holy Trinity's Mission is to challenge and nurture students academically, spiritually, and personally as they prepare for lives of leadership and service.

• 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

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.

• 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.

• 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.

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).

Michael R. “Mike” Truesdell
Senior Consultant
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Tom Lengel
Senior Consultant