Chief of Staff

Position: Chief of Staff
Department: Head of School
Location: Straus, Milton Academy Campus, Milton, MA
Hours: Full-time with the flexibility to work nights and weekends
FLSA: Exempt
Classification: Staff (12 months; flexibility available)

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.”

Summary of Position
Milton Academy seeks a dynamic Chief of Staff to provide strategic & operational support to the Head of School. This individual serves as a trusted collaborator, responsible for shepherding a wide range of initiatives critical to the success of the School, including providing project management & analysis for key projects. The Chief of Staff also supports the Head of School in their communication efforts with key constituencies and organizes materials and next steps related to Leadership Team and Board of Trustee meetings. The Chief of Staff will also ensure that the Head of School’s administrative needs are addressed and that their time can be directed to the most important work of the school.

Essential Functions and Responsibilities

Strategic Planning and Oversight

• Facilitate successful completion of key Board of Trustee objectives, as directed by the Head of School; these may include:
  • Managing strategic planning initiatives, including working with relevant consultants.
  • Documenting goals and action plans related to priorities of the school and the Leadership Team.
  • Tracking the progress of key initiatives being led by others, including Board of Trustee committees, and ensuring delivery of the associated deliverables.
  • Providing timely updates to the Head of School, Board President, and any key constituencies on progress and risks.
  • Editing strategic plan documents for clarity.
• Keep abreast of and research relevant educational trends, policies, and best practices, summarizing potential implications and opportunities for the Head of School.
• Uphold the values of the School and demonstrate a commitment to diversity, equity, and inclusion in all aspects of the role.

Project Management and Analysis

• Administer key projects related to the strategic and operational success of the school, working with the Head of School and associated committees.
• Identify and include key constituencies who should be involved in decision making.
• Manage consultants and/or internal resources to source and produce information as needed.
• Create timelines and ensure deliverables are on-time.
• Assemble, manage and analyze information and data, providing summary conclusions.
• Create presentations.
• Develop agendas and facilitate meetings and discussions as needed.
• Handle project contracts/budgets.
• Contribute to implementing key initiatives in alignment with divisional leadership.

Communication

• Support Head of School communication with various constituencies, including faculty, staff, students, parents, and external partners.
• Prepare presentations and materials as directed by the Head of School, and in collaboration with other departments.
• Attend meetings, presentations, and other community events as requested.

Administrative Support

• Create meeting agendas, draft correspondence, and organize meetings and events.
• Consolidate and assemble board materials.
• Attend all board meetings and create brief and timely minutes to be sent out within two to three weeks of meetings.
• Ensure strategic and best use of the Head of School’s time.
• Other administrative duties as assigned.

Other Professional Expectations and Responsibilities

• Be a visible, accessible presence on campus.
• Work cooperatively with students, parents, peers, administration, and community members.
• Act in a manner that is respectful, generous toward others, supportive of colleagues, and rooted in a belief in the competence and good intentions of all members of the community.
• Communicate openly and promptly, supporting colleagues, students, and the integrity of the institution in conversations with students and parents.
• Contribute to maintaining an environment that is open and flexible, reflecting the school’s values related to diversity, equity, and belonging.
• Strive to grow and improve professionally, demonstrating a commitment to continuing professional development in alignment with the upper school’s growth statements.
• Exhibit skills in collaborative problem-solving, critical thinking, and teamwork.
• Meet deadlines.
• Attend all school-wide, divisional, and faculty meetings and events and serve on committees as required.
• Prepare for and participate in opening-of-school programming, family visit days, graduation, and all other key student/family moments that are part of the school calendar.
• Complete school-required training.
• Abide by the school’s policies and procedures as outlined in the provided handbooks.
• Communicate with the appropriate supervisor when unable to meet any professional obligation.

Supervision to be received: Supervised by the Head of School.

Supervision to be exercised: None.

Education/Certification/Licensure

Required: A bachelor's degree in education, public policy, business, administration,
or a related field

Preferred: A master’s degree in leadership or management - education, public policy,
business, administration, or a related field

Experience

Required:

• A minimum of three years of proven experience in educational leadership, administration
• Experience creating executive-level presentations
• Analysis skills, including the ability to distill key findings from data
• Project management skills, including the facilitation and management of working groups

Preferred:

• Experience working in an independent boarding / day school
• Experience managing consultants
• Experience working with a board of trustees and trustee committees

Competencies

Required:

• Ability to provide strategic direction and guidance, inspire confidence, and lead teams toward common goals.
• Excellent verbal and written communication skills, with the ability to convey complex information clearly and effectively to diverse audiences.
• Capacity to think critically, analyze problems, and develop innovative solutions to advance the mission and vision of the school.
• Strong interpersonal skills and the ability to build and maintain positive relationships with faculty, staff, students, parents, alumni, and other constituencies.
• Demonstrated ability to work collaboratively across divisions and teams to achieve organizational objectives and foster a culture of teamwork and cooperation.
• Proficiency in managing complex projects from conception to completion, including planning, budgeting, execution, and evaluation.
• Strong organizational skills and attention to detail, with the ability to prioritize tasks, manage multiple responsibilities, and meet deadlines in a fast-paced environment.
• Flexibility and resilience to navigate change, ambiguity, and unexpected challenges effectively while maintaining a positive attitude and focus on results.
• Commitment to upholding the highest ethical standards and promoting integrity, fairness, and accountability in all aspects of the role.
• Awareness of and sensitivity to issues of diversity, equity, and inclusion, with the ability to foster a welcoming and inclusive environment for all members of the school community.
• Demonstrated computer expertise, including proficiency in Google Workspace, Microsoft Office (including word, excel, and powerpoint) and Adobe Creative Cloud.
• Commitment to confidentiality and discretion.
• Receptive to supervision and professional development.
• Desire to be a part of a dynamic educational community.

Physical Abilities

Required:

• 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.

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.