Executive Director

About Castle Square Tenants Organization

The Castle Square Tenants Organization (CSTO) is a 501(c)(3) nonprofit, resident-led organization serving the communities of Castle Square Apartments and Eva White Apartments in Boston’s South End. Founded in 1987 as a grassroots tenants organization, CSTO has grown into a significant community-based nonprofit and affordable housing owner while staying rooted in resident leadership and the needs of low-income families and individuals.

Today, CSTO is the majority owner of both Castle Square and Eva White Apartments, in partnership with WinnCompanies. Together, the two properties include about 600 affordable homes. CSTO has an annual operating budget of about $2.5 million, and 20-24 full- or part-time staff members. In addition to its housing responsibilities, CSTO provides a wide range of programs and direct services for children, youth, families, adults, and seniors, including education, technology, workforce development, and resident support programs. CSTO works closely with residents, public agencies, funders, community organizations, and housing partners to preserve and improve affordable housing, expand opportunities for residents, and support a healthy, welcoming, and multicultural community.

About the Opportunity

CSTO is much more than a resident services organization. As the majority owner of major affordable housing properties, CSTO helps oversee the long-term financial and physical condition of its housing, takes part in major renovation and development projects, and works with development partners to preserve and expand affordable housing opportunities. This combination of resident leadership, community programs, and affordable housing ownership makes CSTO a unique organization in Boston.

The Executive Director serves as CSTO’s chief executive and provides overall leadership for the organization. Working with the Board of Directors and leading an experienced staff team, the Executive Director is responsible for making sure CSTO’s programs, finances, staff, housing responsibilities, partnerships, and internal systems work well together and support the organization’s mission. The Executive Director supervises and supports staff, works closely with property management and development partners, consultants, and other professionals, and maintains strong relationships with residents and the broader community.

This is an opportunity to lead a large, resident-led organization that combines community programs and services with ownership of major affordable housing assets and the potential for continued growth in housing, programs, and community investment.

Key Responsibilities:

Governance & Board Relations:

Serve as the primary liaison to the Board of Directors and ensure the Board receives timely, accurate, and useful information.

Carry out Board policies, priorities, and decisions in partnership with staff.

Ensure preparation of clear reports, analysis, and recommendations for Board meetings.

Maintain open communication with the Board about organizational performance, risks, and opportunities.

Strategic Leadership:

Lead the development and implementation of multi-year strategic plans with the Board and staff.

Ensure that programs, staffing, and resources are aligned with CSTO’s mission, community needs, and funding opportunities.

Monitor external trends and policy changes that may affect CSTO.

Guide organizational improvement, innovation, and long-term growth.

Financial Management & Compliance:

Provide overall oversight of budgeting, financial planning, cash flow, and internal financial controls, working closely with staff and outside financial professionals.

Ensure that CSTO meets federal, state, and local requirements, grant conditions, and audit standards, and that regular financial reports are provided to the Board and funders.

Ensure effective management of contracts, procurement, and reporting requirements.

Support long-term financial stability by overseeing fundraising strategy and supporting staff in grant writing and other fundraising efforts.

Development Projects and Asset Management:

Work with CSTO staff, the Developer Partner, and other partners to plan and carry out projects that strengthen Castle Square and Eva White, improve resident services, and support long-term community stability.

Provide oversight of CSTO’s role in the financial and physical management of its housing properties, working with the Management Company and Developer Partner.

Work with the Board and Development Partner to explore appropriate new real estate and affordable housing opportunities beyond Castle Square and Eva White.

Staff Leadership & Organizational Culture:

Lead, support, and supervise senior staff and ensure effective management of staff, consultants, and contractors across the organization.

Set clear expectations for performance, accountability, communication, and documentation.

Build a workplace culture based on equity, respect, teamwork, transparency, and continuous learning.

Program Oversight & Quality Assurance:

Provide overall oversight of CSTO’s programs and ensure they meet enrollment goals, contract requirements, and quality standards.

Work with the Director of Community Programs and other staff to support strong program design, curriculum, and learning outcomes.

Ensure program performance is regularly reviewed using data and resident feedback, and support staff in making improvements when needed.

External Relations & Advocacy:

Represent CSTO with funders, partners, public officials, and community stakeholders.

Provide leadership on advocacy efforts that support CSTO’s mission and help secure resources for the organization and community.

Oversee public communications, media relations, and crisis response, with staff and outside support as appropriate.

Build and maintain partnerships that strengthen CSTO’s programs, housing work, and community impact.

Operations & Infrastructure:

Provide overall oversight of administrative systems, technology, facilities, and day-to-day operational systems.

Ensure staff have the systems, tools, and support needed to operate efficiently and effectively.

Guide improvements that strengthen accountability, coordination, and service quality.

Qualifications:

• Bachelor’s degree required; Master’s degree preferred.
• 5-7 years of progressive leadership experience in nonprofit management, youth development, education, or community programs.
• Demonstrated expertise in strategic planning, financial oversight, staff supervision, and compliance.
• Commitment to improving the lives of low-income residents and community betterment
• Ability to work collaboratively with multi-ethnic and multicultural organizations and individuals of diverse backgrounds
• Excellent organizational and leadership skills
• Excellent written and verbal communication skills
• Extensive knowledge of non-profits operation, compliance and finance
• Working knowledge of affordable housing policies and practices
• Ability to support and work well with others in a high-fast paced environment
• Strong interpersonal skills with a community approach
• Demonstrated experience in community or corporate partnership building
• Exceptional communication, analytical, and problem‑solving skills.
• Commitment to equity, social justice, and community empowerment.
• Proficiency in Chinese language a plus
• Experience in tenant/community advocacy is a plus
• Proficiency in Microsoft Office Suite and/or Google Workspace

CSTO offers a competitive benefits package.

Proficiency in Chinese language a plus