Chief of Staff

Located in Waltham, Lincoln, and Wayland, Massachusetts, Carroll School is an independent day school that serves students with language-based learning differences, such as dyslexia, grades 1-9. Carroll School empowers children to become academically skilled students who are strong self-advocates and confident lifelong learners prepared to enter other academic settings. Carroll 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.

Creating a diverse workforce and an inclusive workplace is an important part of our mission that fosters greater creativity, innovation, and connection to the communities we serve. That mission starts here by building a robust, diverse talent pool. No matter what makes you uniquely different - size, color, culture, gender identity and expression, beliefs, religion, age, race - know that you are welcome here. Your difference makes Carroll stronger.


Research shows that people from underrepresented groups apply to jobs only if they meet 100% of the qualifications. Carroll School encourages you to break that statistic and apply as it's rare to find applicants who meet all the qualifications. We look forward to receiving your application.


Carroll School is an equal opportunity employer that offers competitive salaries and benefits, including comprehensive professional development opportunities.


Position Summary

The Chief of Staff is a strategic partner to the Head of School and a key connector between the Head, the Board of Trustees, and the senior leadership team. Reporting directly to the Head, this person helps translate the school's strategic priorities into coordinated action and ensures the Head's time and attention are directed where they matter most.

The ideal candidate is a sophisticated, discreet, and highly credible leader who can anticipate issues before they surface, synthesize complex information into clear recommendations, and move projects forward across and among teams. They exercise sound judgment on urgent and sensitive matters, know when to act, escalate, or delegate, and build trust with trustees, school leaders, employees, and families. Carroll is a close, relational community, and this is an in-person role.


Key Responsibilities

Strategic Partnership with the Head of School

• Serve as a trusted advisor, offering candid perspective, context, and recommendations on priorities, decisions, and communication
• Manage the Head's agenda and calendar strategically, aligning their calendar with the school's top priorities
• Prepare the Head for high-stakes meetings, conversations, and presentations with briefing materials, background research, and talking points
• Anticipate emerging issues and opportunities, and flag them early with options for how to respond
• Act as a confidential first point of contact for urgent and sensitive matters, using judgment to resolve, escalate, or route to the right person

Board of Trustees Partnership

• Serve as the primary liaison between the Head, the Board Chair, and trustees, ensuring clear, timely, and consistent communication
• Partner with the Head and Board Chair to set agendas and shape board meeting content, so that time is spent on strategy and governance rather than reporting
• Coordinate materials and logistics for all board and committee meetings, special sessions, and retreats, and ensure thorough follow-through on decisions and action items
• Lead implementation and maintenance of board management tools and the trustee portal
• Partner with the board secretary to ensure accurate minutes and institutional records

Institutional Leadership and Alignment

• Partner with the senior leadership team to keep strategic priorities aligned, deadlines met, and cross-departmental work coordinated
• Lead special projects and strategic projects on behalf of the Head, from scoping through completion, collaborating with offices across the school
• Serve on cross-departmental committees and working groups as directed by the Head
• Provide leadership, guidance, and support to campus administrators across all buildings, fostering a sense of belonging and building a strong collaborative community

Community Engagement and Communications

• Help shape and support the Head's engagement with families, employees, donors, alumni, and external partners
• Partner with Advancement, Admissions, Communications, and other teams on events and community-wide moments, ensuring the Head's role is well-prepared and purposeful

Operations and Budget

• Manage the budgets for the Head's office and the Board of Trustees
• Oversee the operations of the Head's office, including calendar, travel, and event logistics, directing or supporting administrative support as appropriate

Requirements

• 5+ years of progressively responsible experience in a chief of staff, executive office, board relations, or comparable strategic role; independent school, nonprofit, or other mission-driven setting strongly preferred
• Demonstrated ability to work as a trusted partner to senior executives and boards
• Excellent communication and relationship-building skills
• Unwavering discretion and sound judgment in handling sensitive information.
• Proven ability to lead projects from inception to completion across a complex organization; highly skilled user of project management and similar productivity technologies
• Success leading cross-functional teams
• Comfort with ambiguity, change, and competing priorities in a fast-paced environment
• Ability to work evenings and weekends as needed, including board and community events
• Bachelor's degree required

Compensation

Target compensation is $120,000; range is $110,00-125,000

Exact salary offered is dependent on experience and demonstrated expertise