Hotchkiss, an exceptional independent boarding high school in the Northeast, seeks an inspiring and action-oriented Dean of Student Life to join its spirited and joyful community family and lead with impact.

Located in the beautiful, scenic Berkshire-Taconic landscape, in the quiet northwest corner of Connecticut, The Hotchkiss School is a diverse and inclusive community in which to live, learn, and grow. The new Dean of Student Life will drive the culture of the School — building an expansive spirit that strategically bridges Hotchkiss’s love of learning, values, sense of responsibility, well-being, and joy into the fabric of the school’s policies, programs, and services.

Reporting to the Associate Head of School, the Dean of Student Life leads the team of professionals responsible for student affairs outside of academics. The Dean of Student Life should possess a balance of superior leadership and personal humility and exercise excellent judgment and communication skills.

Hotchkiss is an inclusive and warm learning community, serving a diverse student body that includes residential borders from 27 countries, 36 different states in the U.S. and 39 percent of students of color. The Dean of Student Life will be a visionary leader and activator who is adept at building authentic relationships and fostering a sense of belonging within Hotchkiss’s diverse community.

The Position

The Dean of Student Life (DSL) is an essential member of the Leadership Team whose strong presence, communication, decisiveness, and problem-solving skills set the tone and strengthen the culture of the School. The Dean is responsible for the planning and implementation of policies, programs, and services that enable and support student learning and growth while maintaining and enhancing student safety and wellbeing. The Dean oversees all aspects of student life, supporting a student life program that fosters a sense of belonging, inclusion, safety, trust, and respect among students in an intentionally diverse residential community. The ideal candidate is a courageous leader and community builder with high EQ, who employs a systems-minded approach. The person is also a student-advocate who inspires, empowers, and brings people together. This multi-faceted and transformational role requires superb commitment, joie de vivre, and a genuine love of students to shape change and sustain growth. It is vitally important that the Dean has an appreciation and well-developed awareness of how differences in students’ backgrounds and experiences influence learning and living in a vibrant, fun, safe, and welcoming community.

Reporting to the Associate Head of School, the Dean of Student Life leads the team of professionals responsible for student affairs outside of academics. The Student Life Team includes administrative assistants, the Associate Dean of Student Life, the Class Deans, the Director of Student Activities, and Dorm Heads. These roles are responsible for the discipline system; advising; the residential life structure and program; student leadership development; and student culture in general. The Dean of Student Life should possess a balance of superior leadership, personal humility, and exercise excellent judgment and communication skills.

Strategic Opportunities

Hotchkiss is looking for a champion for adolescents who is a culture-shaper and compelling leader who will bring people together with positive energy. Through creating enduring relationships as well as equity-focused systems, the Dean will nurture unique opportunities beyond the classroom — building trust, shared purpose, and high community standards. The Dean is the central figure in the daily life of students. The Dean’s work is rooted in cultivating an inclusive community that promotes equity, justice, and cultural competency through courageous decision-making. Guided by transparency, inclusivity, fairness, and accountability, the Dean is responsible for nurturing wholly developed learners who are future-ready, compassionate global citizens, and empathetic community leaders.

Thus, the strategic priorities for this position include the following:

  • Set the vision, direction, tone, and structures for establishing and maintaining a world-class residential student life program that fosters a learning environment and experience where students can have fun and feel safe, heard, seen, and valued.

  • Demonstrate a growth mindset and proficiency for forward-thinking that provides structural support, solution-oriented leadership, and the capacity to nurture buy-in and bring all stakeholders along with a journey of change.

  • Strategically develop policies, procedures, and systems as the front-line leader that guides faculty and creates shared ownership of the community.

  • Create and implement innovative approaches and systems to navigate adolescent tensions with responsibility, freedom, and wellness — which include but are not limited to discipline, residential life, emotional/mental health — and articulately and effectively communicate these policies and procedures to all stakeholders in the community.

  • Work collaboratively with inter-departmental teams to hear diverse thoughts, examine equity in policies, and ensure the best practices in the school experience and residential life programs.

  • Employ systematic support and research-based practices to address socio-emotional challenges students face while also creating opportunities to nurture students’ mental health and build community spirit.

  • Examine the effects of the dual pandemics on student life, and prescribe solutions to address current and perceived needs to come.

Essential Functions

Responsible for all student affairs outside of academics, the Dean is tasked with overseeing, implementing, evaluating, and making informed decisions regarding: the discipline system; advising; the residential life structure and program; student leadership development; and student culture in general.

The essential responsibilities for the Dean of Student Life include the following:

  • Oversee the day-to-day student life and experiences to ensure students’ wellness, mental health, personal growth, community engagement, socio-emotional development, and safety.

  • Work in partnership with Associate Head of School/Dean of Faculty to ensure faculty are trained in, compliant with, and held accountable for the School’s student-centered and mission-focused responsibilities.

  • Proactively create systems that reflect the School’s mission and values, support faculty, and promote a community spirit among students.

  • Lead, train, and empower faculty with the tools and professional habits to cultivate a sustainable culture where students feel safe, seen, and supported.

  • Work in partnership with the Associate Head of School/Dean of Faculty to ensure that appropriate policies, procedures, training, and implementation are in place and effective, both in terms of educational impact and risk management.

  • Build authentic relationships with individual students, student leaders, and affinity groups that encourage cohesiveness, agency, voice, equity, and an inclusive culture while also maintaining healthy professional boundaries.

  • Facilitate and lead weekly student support meetings with interdepartmental teams to proactively address students’ needs and crisis management as appropriate.

  • Oversee advisory programs, discipline, residential life, and student management.

  • Collaborate with the Dean of Academic Life, the Director of Diversity and Inclusion, and the Student Life Team to support the work of Advisors.

  • Collaborate with the Chief Communications Officer to develop a communication plan that serves families and relevant stakeholders, serving as the key administrative contact about School values, expectations, and policies.

  • Work in partnership with the Dean of Academic Life, the Health Center Team, and Class Deans in overseeing on-and off-campus health leaves.

  • Assist colleagues on the Community Conduct Council in upholding the School’s Code of Ethical Conduct.

  • Promote an inclusive working environment, team collaboration, service synergies, and accountability across the community environment.

Qualifications and Requirements

In addition to the qualities and skills noted above, the ideal candidate will possess and have demonstrated:

  • Genuine enjoyment of and effectiveness in working with adolescents and their families.

  • Master’s degree or higher.

  • Substantial administrative leadership experience is required, including responsibility for strategic planning, program and department development, hiring, evaluation, and budget-making.

  • Experience in leading with diplomacy and fortitude.

  • Significant experience working across diverse cultures and leading efforts to create and sustain a more inclusive learning community, including the professional development of administrative and faculty colleagues.

  • Significant professional development in DEIB/J as well as deep personal equity work.

  • Significant experience leading residential life planning and programming, including student leadership and staff development, as well as planning for new and renovated residential facilities.

  • Significant experience designing and implementing programs to promote student leadership development and civic engagement.

  • Excellent management skills, including the ability to delegate appropriately and guide colleagues’ individual professional growth.

  • Excellent communication skills and a collaborative spirit. Effectiveness in managing complex tasks and programs, solving problems, prioritizing among competing demands for time and attention, and driving projects to completion.

  • Enthusiasm for all aspects of the School’s co-curriculum, including athletics, the arts, and student clubs and organizations.

  • Capacity to inspire and guide as well as the humility to listen and learn from others.

  • Experience as a teacher and administrator with a sound knowledge of boarding school life.

The Hotchkiss School is an independent boarding school located in Lakeville, Connecticut. Founded in 1891, the School provides an education of academic distinction to 600 students in grades 9 through 12 and to a small number of postgraduates. Students at Hotchkiss come from across the United States and around the world. Graduates attend many of the most selective universities and colleges.

The Students/Campus Life

Hotchkiss is a diverse community. Small class sizes and an atmosphere dedicated to learning and personal growth make a Hotchkiss education truly unparalleled. On this thriving campus, students have the unique opportunity to share life together as teammates, classmates, friends, and community members.

Community Life

Boarding school campus life at Hotchkiss is characterized by a sense of community. Members of this community are all in it together. They study hard, rest well, overcome challenges, and make memories together. You’ll discover a continual energy — for learning, discovery, and growth — that keeps the Hotchkiss campus vibrant.

As a learning community, Hotchkiss is known for:

  • Team spirit: The nature of a boarding school inevitably bonds people closely together. With over 95% of the students residing in the dormitories, Hotchkiss students form lifelong friendships and make lasting memories together. From the classroom and theater stage to the athletic field and great outdoors, they share every aspect of life together.

  • Diversity: Hotchkiss community life is deeply enriched by the diverse backgrounds of its student body. Its population is comprised of students from a range of nationalities and races, as well as a broad range of socioeconomic backgrounds. Each student brings their own interests, experiences, personality, and skills, creating a diverse and exciting tapestry.

  • Significant financial aid: The School’s goal is to offer quality education that challenges students to reach their full potential. To bring the best students together, Hotchkiss offers generous financial aid packages. Currently, 29% of Hotchkiss students attend tuition-free, and the School is committed to increasing this percentage.

The Faculty and Staff

At Hotchkiss, you’ll find more than 150 faculty members dedicated to mentoring, teaching, and preparing each student to excel at the School and beyond. Each faculty member is committed to going above and beyond their classroom time to support student life, whether through coaching, advising, club mentorship, or college advising.

Hotchkiss teachers have an incredible amount to offer every Hotchkiss student — 72% of faculty hold advanced degrees, and the average faculty member has more than 22 years of experience in education.

Diversity and Inclusion at Hotchkiss

In a truly equitable and inclusive community, the School is greater than the sum of its parts. At Hotchkiss, students of all races, ethnicities, socioeconomic backgrounds, gender identities, sexual orientations, religions, and philosophical and political backgrounds live, learn, create, grow, and have fun together. Fostering a truly equitable and inclusive community requires dedication, and the School’s work to achieve this end goal is ongoing.

To learn more about Diversity, Equity, and Inclusion at Hotchkiss, click here.

The Campus

Located in Lakeville, Connecticut, The Hotchkiss School sits on 827 acres of woods, fields, and farmland in the midst of the scenic Berkshire-Taconic region — a place the Nature Conservancy calls “one of the most extraordinary landscapes in the Northeast.” The School’s state-of-the-art facilities, combined with these surroundings, make Hotchkiss an extraordinary place to live and learn.

The location of the campus allows students to explore an idyllic intersection between nature and community. Surrounded by beautiful greenery and the fresh air of the Northeast, Hotchkiss encourages students to cultivate a healthy love of the outdoors. Their Fairfield Farm gives students a space to explore, hike, and farm food for the school. Students can also embrace the great outdoors right on their doorstep with the walking trails and freshwater lake located around campus.

The heart of Hotchkiss’s campus, however, isn’t the state-of-the-art athletic facilities or renowned academic buildings. While Hotchkiss is proud to be a boarding school with top facilities, the true epicenter of the community lies within the dormitories. Thirteen on-campus residence halls create a homelike atmosphere for students to rest, socialize, and study as they create a home away from home, providing an opportunity for the new Dean of Student life to foster an even stronger and more differentiated student life experience.

Procedure to apply


Priority Application Due Date
March 15, 2022

Semi-finalist Interviews
Late March, 2022

Finalist Interviews
Early April, 2022

Mid April, 2022

*Approximate dates subject to change

Hotchkiss Athletics
Hotchkiss Community Life

Interested candidates are invited to submit the following materials confidentially as one PDF file:

  • A cover letter that addresses interest in working at Hotchkiss with particular focus on the ability and interest in participating fully in an intentionally diverse and inclusive residential community

  • Résumé/CV

  • Statement of leadership philosophy

  • Relevant college and graduate school transcripts

  • Contact information for three references

Please direct any questions via email to or by phone at 415-881-7105.

The Hotchkiss School is an equal opportunity employer and is committed to basing judgments concerning the employment of individuals upon their qualifications and abilities. The School is firmly committed to equal employment and advancement opportunities for all employees and applicants in all phases of the employment process (including recruitment, hiring, assignment, terms and conditions of employment, compensation, benefits, training, promotion, transfer, discipline and termination). In accordance with applicable law, the School does not discriminate against any individual based on age, ancestry, color, genetic information, learning disability, marital status, past or present history of mental disability, national origin, physical disability, race, religious creed, sex, pregnancy, sexual orientation, gender identity or expression, veteran status, or any other protected characteristic.

Unique educational opportunities beyond classroom & pursuit of excellence