Assistant Head of School for Strategy and Operations

Administrator / Full-Time

Carroll School, Lincoln, MA

The Opportunity

Carroll School has a clear mission and a focused program design which allows it to consistently empower children with language-based learning differences, such as dyslexia. The 455 elementary and middle school students in grades 1-9 who attend this independent day school are supported to become academically skilled students who are strong self-advocates and confident life-long learners. The 200 adults employed in this collaborative effort bring deep expertise and empathy to their work. The specialty skills of staff and educators are in high demand; there is a strong waitlist of families who wish to enroll.

The school’s highly engaged board leads collaboratively with the school administration, often sharing a first hand appreciation for the impact of a world-class school that can deliver transformative shifts in academic achievement, self-advocacy, personal growth, and life success for these students. The board’s exercise of its fiduciary responsibility across the school’s 56 years shows in the learning spaces and facilities on three separate campuses, the growing $50 million endowment that reflects the school’s ongoing commitment to financial assistance, and the strategic design and plan.

This community is not simply committed to fostering a sense of belonging across differences, but also inherently curious about how people learn and grow. That exploration is now also a focused effort generating novel and actionable insights on how learning-to-read happens in different brains. The research and technology innovation happening on-site aims to inform and help shift teaching practices beyond campus. Recent recognition in the media that schools everywhere need to address barriers to literacy like dyslexia reflects a marketplace that is ready for new ideas and products. Early collaborations offer proof of concept for how to share what is already happening at Carroll with educators elsewhere.

Having doubled enrollment in the past decade, the school is preparing for another stage of growth and evolution. Head of School Renée Greenfield, a dynamic people-first leader and educational innovator in her 3rd year in that role, is seeking a true partner: an agile strategic, finance, and operations leader. Together, they will engage the board, school leadership, and staff in charting the future of the school and executing on the vision, as the widely respected and effective incumbent strategy and operations leader retires in June after ten years of service.

To find out more about the school and its priorities, please see the head of school’s 2022 entry report (PDF), a Carroll School online magazine issue on what belonging means here, and visit

The Position

Overseeing a professional, collegial, and high performing group of 6 direct reports and a team of 25 overall, the Assistant Head of School for Strategy and Operations is responsible for all financial, administrative, and operational aspects of the school. The established mandate and expectation of the community for the Assistant Head is to create the conditions for a successful learning environment and a resilient community by bringing a strategic, equitable, and business-minded lens to decision making.

The Assistant Head will build relationships, prioritize and anticipate needs, and use collaborative approaches to bring data-informed creative solutions into practice.

This position requires superb relationship management and organizational skills. The successful candidate will have a demonstrated and unfailing commitment to honesty, confidentiality, respect, and the values of the school. We expect the below attributes to guide our exploration of each candidate’s approach to the work. The person in this role will be called upon to:

  • demonstrate the ability to change direction and multi-task as circumstances warrant and to recognize the benefits of different perspectives.
  • analyze, think creatively, synthesize, and effectively allocate resources to the highest priorities and complete projects on schedule.
  • gather information, see all perspectives, make good recommendations and decisions and accept responsibility for results; and exercise sound judgment even when dealing with emotionally charged topics.
  • objectively assess and respond to difficult workplace situations, appreciate differences in lived experiences, foster a positive atmosphere, and maintain a sense of humor.
  • demonstrate a commitment to equity, belonging, professional growth. Model a growth and learning mindset.

Putting people first, and modeling for others what that looks like, is the priority.

Key responsibilities

1) Develop, implement, and oversee plans and programs in the key functional areas of:

  • Finance, including budgeting, reporting, and endowment management
  • Human resources, including compensation and benefits
  • Risk management, including legal matters
  • Campus planning and facilities management
  • Technology

2) Collaborate with the Head of School, board of trustees, board committees and the senior leadership team to realize the school’s strategic priorities.

3) Manage six direct reports who oversee the finance, information technology, facilities, human resources, cognitive intervention, and nursing departments.

In conjunction with the Chief Financial Officer, prepare, present, and monitor long and short term operating and capital budgets. Work closely with the finance and investment committees of the board of trustees. Conduct benchmark analyses when making budget recommendations. Actively engage with other independent school leaders to incorporate best practices in the work. Ensure that the School’s long term financial health is understood and a priority.

In conjunction with the Director of Facilities, work with the facilities and campus planning committees of the board of trustees to add to, improve, protect and preserve the physical assets of the school. Work with the School’s planners/architects and consultants on real estate and construction projects. Ensure that School’s health and safety risks are identified and mitigated. Oversee all major real estate acquisitions and construction projects including contract negotiations.

Work with the Director of Human Resources on all matters of employee relations including hiring, compensation, benefits, and compliance with all state and federal employment laws. Develop, propose, and implement compensation and staffing recommendations as part of planning and budgeting processes. Act as the point of contact with the school’s attorney on legal matters. Advise Head of School on employment and legal challenges.

In conjunction with the Chief Technology Officer, develop and implement best practices in the acquisition and use of technology across all academic and business functions. Ensure that spending on technology is strategically planned and deployed.

Provide ongoing management and support for Neurolution, the school’s ongoing effort to share with other schools, via a technology platform, the cutting edge effort to enhance student’s academic outcomes through targeted cognitive interventions. Partner with the steering team, the head of product, head of school, outside consultants and researchers to advance and fund this undertaking.

Work closely and impactfully with the directors of Enrollment, Financial Aid, Afterschool Enrichment, Summer School, Diversity Equity and Inclusion, Advancement, and Nursing. Actively serve on the financial aid committee. Lead the Health & Safety committee. Help others succeed in their work and deliver positive outcomes for the School.

Support the community of families, students, and employees to the best of one’s ability even when outside the scope of responsibilities. Lead, by example, in the ongoing journey for racial justice, equity, and inclusion of all types of human difference.


The ideal candidate will be an experienced executive and a team player who possesses:

  • An undergraduate degree with an emphasis on strategy and finance. An MBA or significant business education at the graduate level is highly desirable.
  • Ten to fifteen years of related experience in financial and human resources administration, of which five years should be at the management or executive level with a similar breadth of responsibilities. Ability to manage and delegate multiple functions and activities.
  • Familiarity with not-for-profit management, not-for-profit reporting, and human resource policies and practices.
  • Demonstrated strategic planning ability as well as effective interpersonal, organizational, analytical, and communication skills.
  • Ability to remain calm, flexible, and work effectively under pressure.
  • Demonstrated commitment to equitable and inclusive practices.

Carroll School is an inclusive community committed to embracing diverse strengths, identities, and lived experiences in order to give each child what they most need to thrive.

Research shows that underrepresented groups apply to jobs only if they meet 100% of the qualifications. Carroll School encourages you to break that statistic and apply. No one ever meets 100% of the qualifications.

Carroll School is an equal opportunity employer that offers competitive salary and benefits, including a strong professional development program.

Interested candidates, please contact Narwhal Talent Partners:

Peter G. Hamilton  |  (617) 620-9268

Christian G. Henry |  (857) 285-3364

All inquiries are treated as confidential.

Carroll School

Lincoln, MA
Elementary, Middle School, High School
All Gender