Managing Director, Chief of Staff

Overview

ROLE

TITLE:

Managing Director, Chief of Staff

POSITION

REPORTS TO:

Massachusetts Executive Director

Final date to receive applications: Applications are due on June 22, 2026, by 11:59 PM ET.

LOCATION: Massachusetts (Boston)

Teach For America Massachusetts (TFA MA) is seeking a Managing Director, Chief of Staff to serve as a force multiplier for the Executive Director and a central integrator for the region’s operations, culture, and organizational effectiveness. Reporting directly to the Executive Director, this role helps ensure the regional team operates with strong alignment, clear communication, collaborative culture, and effective execution.

The Chief of Staff will serve as a highly trusted strategic and operational partner to the Executive Director and leadership team, helping translate the region’s strategic priorities and new 5-year strategic plan into coordinated action across the organization. This role is designed for a systems-oriented leader who thrives in dynamic environments and can seamlessly move between strategic planning, operational leadership, project management, organizational problem-solving, and team coordination.

The ideal candidate brings strong executive presence, sound judgment, operational rigor, and the ability to manage multiple high-priority work streams simultaneously. They are energized by helping leaders and teams operate more effectively, building systems that strengthen collaboration and execution, and creating organizational conditions where teams and people can thrive.

This is not an Executive Assistant role. While the Chief of Staff will partner closely with the Executive Director’s Executive Assistant and help coordinate executive office operations, the primary focus of the role is organizational leadership, operational systems, team effectiveness, and executive leverage. The role also serves as the primary operational lead for the Massachusetts team’s coworking space, ensuring the physical office environment effectively supports collaboration, culture, and day-to-day operations.

Time allocation percentages reflect primary areas of responsibility.

Executive Leadership & Organizational Alignment (35%)

• Serve as a strategic operational thought partner to the Executive Director, helping drive prioritization, decision-making, and execution across regional priorities and stakeholders (TFA MA Leadership Team, TFA MA Regional Team, National TFA Team, TFA MA Board, Corps Members, School and District Partners, and Alumni)
• Drive our region’s participation in org-wide annual planning, regional strategic plan implementation, OKR management, and organizational accountability processes
• Lead preparation, facilitation, and follow-through for leadership meetings, retreats, step-backs, and key cross-functional initiatives
• Develop executive briefings, communications, presentations, and strategic materials that support leadership engagement and decision-making
• Serve as a connector across teams and functions, helping leaders navigate interdependencies, surface risks, and maintain alignment on priorities
• Support Board operations and strategic engagement in partnership with the Executive Director and Senior Managing Director of Development, including project management, planning, and coordination for quarterly board meetings
• Serve as a flexible strategic and operational capacity for emerging priorities, organizational initiatives, and high-impact projects identified by the Executive Director and leadership team
• Coordinate closely with the Executive Assistant to ensure strong, proactive alignment between Executive Director priorities, scheduling, communications, and organizational follow-through
• Serve as a proxy and representative for the Executive Director, as appropriate, in cross-functional coordination and stakeholder engagement

Design and steward the operational systems, communication practices, and team experiences that enable strong collaboration, execution, and thriving culture across the region.

• Lead and strengthen regional operating systems, workflows, planning processes,…