Career Opportunities with Milton Academy


Careers At Milton Academy

Current job opportunities are posted here as they become available.

Subscribe to our RSS feeds to receive instant updates as new positions become available.

Upper School Dean of Faculty (Internal Only)

Department: 01-51110-501 Us Principal Exempt
Location: Milton, MA

Position: Dean of Faculty

Department: Upper School

Location: Warren Hall, Milton Academy Campus, Milton, MA

Hours: Full-time with the flexibility to work nights and weekends

FLSA: Exempt

Classification: Staff (12-month)

Milton Academy is an independent college preparatory K–12 school, boarding and day in grades 9–12, located just outside of Boston.

Milton Academy cultivates in our students a passion for learning and a respect for others. Milton students grow by developing their own identities, learning from and listening to the lived experiences of others, and living and working among peers whose differences they accept with respect and care.

In our ongoing work to create an environment that confronts bias, injustice, and bigotry, we encourage each other to be open to learning, explore our histories and identities, and seek to understand the world around us with a critical lens. At Milton, we prepare students to partner with their future communities to create a more just world, and to have the courage to speak up and live by our motto, “Dare to be true.”

Position Summary

The Upper School dean of faculty is an administrator responsible for providing leadership and support to the Upper School faculty. Reporting to the Upper School principal, the dean of faculty ensures that all decisions consider the impact on teaching and learning, as well as on faculty members in general. To that end, the dean is a strong listener who dialogues with the faculty as a whole, departments, and individual faculty members as needed. In practical terms, the dean leads the recruitment, hiring, retention, evaluation, and assignment of workload (class and other assignments). The dean also identifies opportunities for the growth and development of faculty, both individually and within departments, and participates in determining professional development fund allocations in collaboration with the teaching & learning team. To accomplish these multi-dimensional goals, the dean oversees and closely collaborates with the division’s department heads (chairs) to ensure that departmental and faculty-related information and needs are well understood and addressed.

The successful candidate will be an experienced teacher respected by their peers, highly collaborative, adept at navigating complex circumstances and conversations, and able to understand how and when to facilitate change and consensus. Ideally, the candidate will also have demonstrable experience in applying, updating and creating faculty-related policies, implementing and/or building performance evaluation systems, and navigating workload-related complexities at private schools.

The school seeks strong internal candidates for this role who could also contribute to the broader student experience, from co-curricular to athletic to residential life programming.

Essential Functions and Responsibilities:

  • Support faculty needs and relations, in collaboration with department chairs, upper school administrators, and human resources.

    • Build and maintain a faculty culture that is supportive of colleagues, provides opportunities for growth, welcomes diversity, fosters inclusion & belonging, and builds community.

    • Ensure that faculty feel heard and responded to; engage with faculty individually as needed.

    • Develop programs, policies and procedures to support, develop, and mentor the faculty and department chairs.

    • Identify goals for the Upper School program, each department, and individual faculty members, in collaboration with department chairs and the academic dean, to ensure a high quality academic program with a focus on continuous improvement.

    • Provide perspectives from the faculty and department chairs when attending divisional and other administrative meetings, including to the school’s leadership team.

  • Lead and oversee in the recruitment & hiring process for Upper School faculty members, in close collaboration with department chairs.

    • Identify potential vacancies and needed resources, in alignment with course planning and projected enrollment.

    • Establish recruiting priorities and plans to source a strong and diverse pool of candidates, in partnership with the human resources department.

    • Create clear job descriptions that set expectations for daily work and highlight specific competencies required for open positions.

    • Ensure that all school recruitment and hiring guidelines are followed as part of the process.

    • Oversee new faculty onboarding and training, also in collaboration with the teaching & learning team and human resources.

  • Oversee and manage the faculty evaluation process, as implemented by the department chairs.

    • Ensure that a clear and measurable evaluation process is in place within the Upper School which reflects the myriad roles that a faculty member may fulfill.

    • Facilitate department chair completion of faculty evaluations on a regular basis; ensure that the evaluations are used to provide affirmation and feedback.

    • Follow up on any identified issues to ensure both individual support and accountability.

  • Facilitate faculty professional growth and learning, working with department chairs and the teaching and learning team.

    • Identify areas of growth for the full faculty, sub-sets of the faculty, and/or specific departments.

    • Ensure that individual faculty members receive feedback on their approach to teaching, both inside and outside the classroom, and are mentored.

    • Collaborate with the department chairs and teaching and learning team in integrating instructional strategies and curricular development based on shared data and standards.

    • Plan agendas for and facilitate regular faculty meetings and professional development days that are aligned with departmental, divisional, and institutional goals.

    • Ensure equitable access to and award of growth grants.

  • Support department heads in the supervision of faculty.

    • Facilitate regular department chair meetings to address questions, surface issues, problem solve, and ensure connections across departments.

    • Be flexible and available to faculty to address situations requiring immediate resolution and attention.

    • In collaboration with HR, ensure that department chairs have clear job descriptions and are trained to mentor and manage faculty.

    • Provide formal and informal feedback and periodic formal evaluations to department chairs to inform their work with faculty and help them grow as managers.

  • Oversee the allocation of workload for the coming school year, in collaboration with the Academic Dean and Department Chairs.

    • Ensure that all core courses required for graduation are available.

    • Prioritize elective courses based on demand and available resources.

    • Work with department chairs to determine when additional workload above baseline levels may be needed and if so, how it will be prioritized given departmental assignments, institutional needs, and limited funding.

    • Issue workload letters for the coming academic year to every faculty member, reflecting classroom, athletic, co-curricular and other assignments, no later than early summer.

  • Serve as a member of the Upper School's Administrative Team, facilitating the achievement of divisional and institutional goals.

  • Perform other duties as assigned by the Upper School principal.


  • Serve as an advisor to a group of up to nine students, engaging in advisor meetings each week.

  • Connect, support, communicate, encourage, and celebrate each advisee.

    • Facilitate students' social-emotional learning and growth in alignment with all school programming through small group meetings.

    • Build deep relationships with each advisee and assist them in navigating challenges they may encounter.

    • Form relationships with and act as a liaison between the school and advisee families; serve as the first point of contact between the school and families.

  • Read and be familiar with all relevant materials, most importantly the Student Handbook and the sections of the US Faculty Handbook on academic regulations and diploma requirements.

  • Be informed about course offerings for the following year and help each advisee select programs that are challenging and appropriate, as well as areas of special interest.

  • Review each advisee’s grades and comments.

  • Craft formal advisor reports for each advisee two times per year, offering overarching perspectives on their progress, and acknowledging a broader view of their academic and community achievements at Milton.

  • Should an advisee need additional support in a particular area, be in steady contact with the advisee’s teachers, administrators, and/or other committees as needed.

  • Attend all upper school student required weekly assemblies, programming, and special events (e.g., community service day, pep rallies).

  • Attend class trips, retreats, and social events arranged by the director of student activities or the class dean.

Residential Life (if residing in on-campus housing)

  • Act as a mentor and role model in all areas of the residential program, demonstrating a commitment to the success of each student, especially in the areas of social and emotional development.

  • Contribute to creating a positive community culture within the dorms that ensures students are heard, seen, valued, and cared for.

  • Be on call (on duty) as a dorm parent in a residential dorm once a week and on rotational weekends and ensure that all responsibilities and rules outlined in the faculty handbook around dorm supervision are adhered to.

  • Facilitate and oversee programming when on duty and supervise recreational activities as assigned.

  • Communicate regularly with other house staff as an opportunity to check in about the students in the dorm.

  • Attend at least two dinners per week with the dorm community.

Additional Responsibilities:

  • Teach one academic class.

  • Serve as a mandated reporter in support of school risk management.

  • Acknowledge receipt, review, and abide and manage by the rules, policies and procedures stated in the current Milton Personnel Policies Manual and Upper School Faculty Handbook.

Supervision to be received: Upper School Principal

Supervision to be exercised: Upper School Department Chairs in collaboration with the Academic Dean and Upper School Principal; Upper School faculty in collaboration with Department Chairs and the Upper School Principal.


Required: Bachelor’s degree

Valid driver's license with at least six years of driving experience

Preferred: Advanced degree, particularly in education or other related field



  • Experience as a secondary school teacher.

  • Understanding of how to support faculty and department chairs in their evaluation and growth.

  • Prior management of programs, departments, or initiatives that demonstrate the ability to work collaboratively and effectively with others.

  • Experience with mentorship and other faculty-supportive programs.

  • Familiarity with workload concepts and challenges.

  • Demonstrated ability to manage and prioritize multiple projects and meet deadlines.

  • Experience in a diverse, multicultural learning environment.


  • Three to five years of experience in a private school management position.

  • Teaching experience at more than one school; recognized as an experienced teacher respected by their peers.

  • Experience with advising, coaching, and/or administration in a private school.

  • Experience in facilitating collaborative discussions and leading change.

  • Experience with faculty evaluation.

  • Experience in a residential school setting.

  • Ability to formulate and articulate sound policies and resolve administrative and personnel issues.

  • Ability to consolidate complex information and data into concise summaries and develop recommendations.



  • Excellent verbal and written communication skills.

  • Demonstrated computer expertise, including proficiency in Google Workspace, Microsoft Office and Adobe Creative Cloud.

  • Ability to work collaboratively with internal and external constituencies.

  • Understanding of confidentiality and related issues.

  • Receptivity to supervision and professional development.

  • Desire to be a part of a dynamic educational community.

Physical Abilities


  • Must be able to work at a computer for up to 8 hours each day in conjunction with OSHA requirements.

  • Must be able to move around the Milton Academy campus without restriction.

  • Must be able to lift up to 10 pounds.

Other required experience and abilities:


  • Motivated self-starter and strategic thinker.

  • Creative problem solver.

  • Exceptional interpersonal and listening skills.

  • A collaborative leadership style that exhibits patience and persistence.

  • High energy, with enthusiasm for residential school life.

  • Models professional and respectful behavior.

All interested internal candidates must complete an application for promotion or transfer and inform your supervisor as soon as possible.

The essential functions and basic skills have been included in this job description; it is not intended to be construed as an exhaustive list of all functions, responsibilities, skills and abilities. Additional functions and requirements may be assigned by supervisors as deemed appropriate. This position description is subject to change at any time.

An equal opportunity employer, Milton embraces diversity and the pursuit of excellence. All qualified applicants will receive consideration for employment and will not be discriminated against on the basis of race (including natural and protective hairstyle), color, sex (including pregnancy and pregnancy related condition), sexual orientation, gender identity, gender expression, religion, religious creed, physical or mental disability, age, genetic information, veteran status, ancestry, citizenship, national or ethnic origin or any other status protected by applicable law.

Applicant Tracking System Powered by ClearCompany HRM Applicant Tracking System