Managing Director, Chief of Staff

ROLE TITLE: Managing Director, Chief of Staff

POSITION REPORTS TO: Massachusetts Executive Director

APPLICATION DEADLINE: Applications are due on June 22, 2026, by 11:59 PM ET.

LOCATION: Massachusetts (Boston)

WHAT YOU'LL DO

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 workstreams 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.

WHAT YOU'LL BE RESPONSIBLE FOR

Time allocation percentages reflect primary areas of responsibility.

Executive Leadership & Organizational Alignment (35%)

Support the Executive Director and leadership team to operate with clarity, alignment, accountability, and strategic focus.

• 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

Organizational Operations, Collaboration & Team Culture (40%)

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, and coordination practices that improve organizational effectiveness

• Design systems and operating rhythms that strengthen collaboration, accountability, communication, and alignment across a hybrid regional team

• Establish structures to monitor progress toward the region's 2031 strategic plan and organizational goals

• Manage high-priority cross-functional projects and operational initiatives from planning through execution

• Lead planning and facilitation for monthly regional team meetings, retreats, onboarding experiences, and staff engagement initiatives

• Partner with regional leaders to strengthen team culture, collaboration norms, staff engagement, and inclusive leadership practices across the organization

• Review team culture and engagement data, and facilitate the adoption of responsive priorities that promote a positive, inclusive, thriving culture

• Develop and maintain dashboards, tracking systems, and operational reporting tools that support organizational learning, decision-making, and communication with staff, board members, and donors

• Support strong internal communication and change management practices so priorities, decisions, and next steps are clearly understood and operationalized across teams

• Identify organizational gaps, friction points, and operational risks, proactively designing solutions that improve effectiveness and team experience

• Serve as a key liaison for regional coordination with National TFA teams, ensuring strong communication, responsiveness, and operational partnership

Administrative Operations & Workplace Management (15%)

Ensure strong operational administration and a high-functioning workplace environment that supports the team's day-to-day experience.

• Oversee workplace operations and serve as the primary operational lead for the team's coworking space at CIC Boston

• Manage office logistics, vendor relationships, supplies, access management, and workplace coordination

• Support operational administration related to budgeting coordination, expense management, invoices, and vendor processes

• Set and maintain a regional calendar accessible to all team members

• Maintain systems for knowledge management, documentation, file organization, and operational continuity

• Lead operational onboarding for all new TFA MA staff members, ensuring regional team members can access TFA systems, technology, and understand operational policies and procedures

• Coordinate logistical support for regional meetings, events, visiting stakeholders, and team experiences

Support Organizational & Regional Stewardship (10%)

• Support, attend, and/or participate in regional and cross-team activities and campaigns, including staff meetings and events (Corps programming, Alumni events, Fundraising events)

• Participate in org-wide initiatives, including corps member matriculation and corps member selection interviews

A WEEK IN THE LIFE

Over the course of a typical week, the Chief of Staff may facilitate leadership team coordination, support strategic plan implementation, manage cross-functional project execution, prepare briefing materials and recommendations for key decisions, and help drive follow-through on organizational priorities. Some weeks may lean more heavily into planning and operational systems design, while others may focus on stakeholder coordination, workplace operations, team culture initiatives, leadership communications, or regional events.

The Chief of Staff regularly operates across strategic and tactical levels of work - shifting fluidly between executive partnership, project leadership, operational problem-solving, and organizational coordination. The Chief of Staff also plays a key role in ensuring the region stays connected and informed through strong communication, consistent operating rhythms, and proactive coordination across teams.

CORE COMPETENCIES TO BE SUCCESSFUL IN THIS ROLE

• Organizing, Planning, and Managing Execution: Skilled at designing and managing systems, cadences, and workflows that maximize organizational effectiveness. Able to think strategically across multiple priorities while also driving detailed execution. Highly effective at prioritizing, coordinating, and managing work across teams and stakeholders.

• Strategic Thinking and Problem Solving: Able to synthesize information, identify patterns and interdependencies, and translate insights into actionable strategies and solutions. Navigates ambiguity effectively and generates thoughtful approaches to complex organizational challenges.

• Sound Judgment and Decision-Making: Uses context, data, and stakeholder perspectives to make thoughtful decisions in dynamic environments. Exercises strong judgment, discretion, and professionalism, including when managing sensitive or confidential matters.

• Influencing and Relationship Building: Builds trust and strong relationships across lines of difference and functions. Demonstrates strong communication and influence skills and can bring people together around shared goals, priorities, and ways of working.

• Cross-Functional Leadership and Collaboration: Proven ability to lead and integrate work across diverse functional areas, balancing multiple stakeholder perspectives while maintaining organizational alignment and momentum.

• Systems Orientation and Operational Effectiveness: Able to design and improve systems, structures, and operating practices that strengthen collaboration, communication, accountability, and execution across teams.

OUR EXPERIENCE

Your areas of knowledge and expertise that matter most for this role (minimum qualifications):

• At least 7 years of related experience in operations, strategy, project management, consulting, organizational leadership, or executive support roles

• Demonstrated success operating with a high degree of ownership and autonomy in complex, collaborative, and dynamic environments

• Strong strategic thinking, operational problem-solving, and project management skills, with the ability to translate vision into execution

• Strong data analysis skills and experience using data-driven decision-making tools and practices to support organizational learning and decisions

• Proven ability to drive cross-functional coordination, manage competing priorities, and build strong organizational systems

• Strong executive presence, judgment, communication, and relationship management skills

• Strong relationship-building skills and the ability to tailor systems, processes, and communication approaches to support collaboration, alignment, and team culture

• Experience managing operational logistics, workplace systems, or hybrid office environments strongly preferred

• Proficiency with collaboration, project management, and communication tools (Google Workspace, Slack, Asana, Airtable, or similar platforms)

• Bachelor's degree required

BONUS (Preferred Qualifications)

• MBA or equivalent leadership, consulting, or operational experience

• PMP, SCRUM, or related project management certification

• Experience of serving in a Chief of Staff, Strategy & Operations, Consulting, Program Management, or equivalent role

• Experience working in education, nonprofit, public sector, or mission-driven organizations

• Experience supporting senior leaders and leadership teams through strategic planning and organizational change

• Experience leading cross-functional initiatives in highly matrixed environments

WORK DEMANDS

• Ability to work occasional evenings or adjusted hours in support of events, leadership meetings, or organizational priorities

• Ability to travel locally within Massachusetts, as needed, for team and stakeholder engagement

YOUR FUTURE TEAM

You will be a core member of the Massachusetts regional team, partnering closely with the Executive Director and collaborating across functions to strengthen organizational effectiveness and regional impact.

The Massachusetts team works collaboratively - and in partnership with students, families, alumni, educators, and community leaders - to advance educational opportunity and systems change across the Commonwealth.

We embrace a hybrid work environment and value clarity, trust, strong relationships, operational excellence, continuous learning, and a deep commitment to educational equity in how we work together.

YOUR COMPENSATION

The applicable salary range for each U.S.-based role is based on where the employee works and is aligned to one of three tiers according to a cost-of-labor index in that geographic area. Starting pay for the successful applicant will depend on a variety of job-related factors, which may include education, training, experience, location, business needs, or market demands.

New hires are typically brought into the organization at a salary between the range minimum and midpoint, depending on qualifications, internal equity, and the budgeted amount for the role.

The expected salary range for this role is:

Tier C Salary: $106,200-$141,900

You can see which salary tier applies to where you plan to work here. If your location is not listed, please click here for additional total rewards information.