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Head of School

Company name
About The Ancona School

Chicago, IL

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Chicago, Illinois




Full Time - Administration


Head of School

Preferred Education:


About the Ancona School

The Ancona School (Ancona) is an independent school located in Chicago’s historic Hyde Park-Kenwood community, educating students 3 years old through 8th grade. Since our founding in 1962, Ancona has been dedicated to diversity in both our community and our curriculum which draws upon the Montessori and Progressive Education models. Social justice education is the cornerstone of Ancona’s mission as a school; it informs what we teach and how we teach it. At every grade level, Ancona students learn to identify inequality and are empowered to address injustice in the world.

School Mission

Ancona educates students to become creative problem solvers, confident risk takers and independent, lifelong learners. Rooted in the Montessori tradition, our child-centered school stimulates the joy of learning and builds a strong academic foundation. We inspire children to nourish their inner lives, find the power in their own voices and strive for justice and peace. In a community of cultural and economic diversity, Ancona cultivates understanding, care and respect for others.

About the Head of School Position

Ancona’s Head of School will set the vision and strategy to achieve the school’s mission and position it for long-term sustainable success. The Head has significant strategic and internal responsibilities, a substantial external focus, and important governance and financial accountabilities. As the school’s professional, institutional, and educational leader, the Head reports to the Board of Trustees but is responsible, as well, to the school’s multiple constituencies – administration, faculty, staff, parents, students, and alumni. Managing the interrelationship and sometimes competing demands of these multiple responsibilities and constituencies is crucial to the Head’s success. The Head builds understanding around the mission and vision of the school and projects a positive public image, embodying the professional profile and exemplifying the School’s warmth in a way that inspires confidence and rapport with all.

The ideal candidate to be the next Head of the Ancona School will be an individual who is passionate about the school’s mission and vision; is cognizant and respectful of Ancona’s tradition of teacher autonomy while proactive in ensuring outstanding teaching; is a visible presence in the school and in the local community; understands the critical role of development and marketing in a successful independent school; and skilled at reaching out to develop relationships with potential donors. They should embody the spirit of “challenge with warmth” that permeates the school and is fostered by faculty and staff. The new Head will demonstrate leadership in partnership with the Board of Trustees and will be skilled in recruiting, hiring, and guiding teaching faculty and administrative staff.

The Position: Specific Duties

1. Stewardship of Ancona’s history, culture, climate, and strategic direction

The Head of School, together with the academic team, supports a culture and professional environment that both maintain continuity with the past and encourage innovation and experimentation on the part of the teachers. They will have a deep understanding of the interplay of historical forces and educational currents that have shaped the school— Montessori-influenced, progressive and child-centered, developmentally appropriate education, experiential education, multiculturalism, racial and social justice, teacher participation, and meaningful parental involvement—and that form the foundation upon which the school will build its next fifty years.


Leadership of a strong educational program that positively engages students as learners

The Head of School approves and works together with faculty to ensure that the School’s entire educational program is coherent across grade levels, and aligned with the school’s mission and best understandings of child development and diverse student learning and behavior needs. In addition, the Head of School, together with the faculty, puts into place comprehensive assessment systems to understand and support student learning and make learning visible to students and parents. The Head of School is known to students as one who takes an interest in their learning and cares about individual student development and achievements as well as the student community at-large.


Support and development of talent to ensure that Ancona is a desired place to teach and work

The Head of School is responsible for retaining, finding, interviewing, and hiring the faculty and senior administrative team. The Head ensures that the school has an excellent work environment, and that faculty and staff know what is expected of them and are engaged in and excited about their work. The Head of School is cognizant and respectful of Ancona’s strong traditions of teacher leadership, creativity, and autonomy, and works cooperatively with academic administrators to ensure that teachers receive the support they need to perform to their highest potential and that the needs of individual children are met. The Head of School maintains warm, open, and friendly relationships with all members of the faculty and is a frequent visitor to classrooms; they can speak knowledgeably and confidently about all aspects of the program.


Engaging parents as partners in their child’s education

The Head of School maintains open, warm, and friendly relationships with parents; helps them to understand and appreciate the Ancona experience, while engaging them as partners to provide the best learning environment for each student and the overall school community. The Head of School also engages parents in key aspects of Ancona’s unique culture, including shared and open dialogue on matters of race and equity, and inspiring parents to bring their time and resources to bear to help the school flourish. The Head needs to be available to parents while also ensuring timely and consistent responsiveness to parents from all administrators and faculty.


Managing the fiscal sustainability of the school

The Head of School works with other administrators to protect and secure the financial well-being of the school. Together with Director of Finance and Operations, the Head plans, manages, and is accountable for the School’s resources, including devising and managing the School’s budget. Ancona has two primary revenue streams: philanthropic support and tuition. The Head serves as Ancona’s chief fundraiser, partnering with the Director of External Affairs to manage Ancona’s fundraising strategy and build awareness of the school and secure the contributed income necessary for the school to fulfill its vision; they devote significant time to seeking and procuring major gifts for the school. In addition, the Head collaborates with the Director of Admissions and regularly engages in personal and energetic recruiting of families.


Effectively overseeing and collaborating with the Directors of the school

The administrative team is charged with the responsibility of shaping an educational environment that implements the philosophy and values of the school in an efficient, effective business environment. The Head of School partners with the administrative departments heads on the operational execution and the overall management of the school and long range strategic planning. The Head of School leads the senior administration team, operating collaboratively and with open discussions on a regular basis. The Head must give these professionals the latitude to execute while ensuring that activities are coordinated and consistent with plans and school policies.


Board engagement and education

The Head has a dynamic relationship with the Board of Trustees, serving as the Board’s only employee, while also educating the Board on the nature of independent school governance and the Board’s powers, responsibilities, and limits. The Head of School’s responsibilities to the Board include recommending policies, reporting on budgetary matters, and providing an accurate profile of the entire school program. The Head attends all Board meetings, serves as staff to the Executive Committee and Committee on Trustees, and is an

ex officio

member of every Board committee.


Engaged communication and partnership across various constituencies

The Head must maintain a high level of visibility within the school community. The Head serves as the school’s chief communicator, an articulate and effective spokesperson, as well as a savvy negotiator who is well-apprised of the particular economic, political, and social structure of the community. The Head’s leadership presence and communication capabilities engender the trust and good will of the entire school and the public. As part of this, the Head of School partners with the Director of External Affairs to ensure that the mission and vision for the school are progressing with regular opportunities for authentic conversation, input, and shared discussion with various school constituencies. The Head of School participates in all faculty meetings; keeps faculty and staff apprised of school developments; and elicits their ideas, questions and concerns. The Head also partners with the Marketing and Communications Manager to manage Ancona’s communications efforts and public presence through the school’s website and social media.

Key Competencies

The ideal candidate will demonstrate some or all of the following:

Instructional Expertise

Uses an understanding of research and best practice in education to support the design and implementation of a coherent instructional program aligned to standards (aligned curriculum, assessment, instruction, and intervention) that is accessible to all students, and cognizant of diverse learning and behavioral needs

Understands and can teach others the principles of lesson design, based on the needs of individual learners

Understands and can teach others how to use culturally and linguistically responsive instructional strategies that engage, challenge, and build learner independence

Talent Development

Anticipates staff turnover, plans recruitment to fill positions early, and continually strengthens the skill sets represented across faculty

Uses student, classroom, and school data, along with school improvement priorities, to identify high-leverage professional learning opportunities for individual teachers, collaborative teacher groups, and the whole school

Creates regular opportunities for teachers to learn from and with one another, including opportunities to observe, analyze, reflect upon, and refine their teaching practices in teacher-led, collaborative groups

Distributes leadership across the school, systematically leveraging staff members’ strengths, experiences, and demonstrated success with students to advance school goals and build leadership capacity of staff

Relationship Building and Communications

Communicates clearly and persuasively with diverse individuals and stakeholder groups, tailoring messaging, medium, frequency, and scope as needed to ensure that communication is accessible and responsive to audiences with different backgrounds and perspectives

Creates conditions for an inclusive and culturally responsive school climate that is based on trusting relationships among students, parents, staff, and community

Establishes a school culture that values creativity and innovative problem solving, encouraging imaginative thinking and new ways of personalizing learning for all students

Develops and implements systems to generate feedback from stakeholders that results in improved school performance

Anticipates and effectively manages conflict, using active listening and conflict-management skills to proactively resolve disagreement among stakeholders

Strives to reach consensus, but recognizes that it is not always possible and manages change process to keep school moving on important priorities

Confronts preconceptions around race, culture, class and other issues of difference; models open dialogue and initiates difficult conversations on these topics with staff, students and the community

Experience Preferred

10 years of progressive experience in academic settings as a teacher, department head and/or administrator

5 years’ experience in a comparable senior leadership position with a successful track record

Experience leading, managing, and coordinating a broad range of academic functions in line with strategic objectives

Operational and financial management experience

Experience in fundraising

Education Preferred

Doctoral degree in a related discipline preferred

Master’s degree in education

An outstanding academic background


Additional Salary Information: Salary for this position is competitive and commensurate with prior experience. In addition, a comprehensive benefits package is included.

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About The Ancona School

The Ancona School is a 21st century independent school for preschool through 8th grade students located in Chicago's historic Hyde Park-Kenwood community. Since its founding in 1962, Ancona has been a leader in providing a thoughtful, experiential and multicultural education to a diverse population of learners. The school combines the best of Montessori and progressive educational traditions with

innovative teaching and curriculum in open, multi-age classrooms. Ancona graduates go on to Chicago’s most selective public, independent and parochial high schools. Outstanding teachers, active parent involvement and a true concern for social justice distinguish our community of learners.

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