Senior Director of Permanent Supportive Housing

Job Title:

Senior Director of Permanent Supportive Housing 

Reports To:

Chief Operation Officer

Location:

Boston, MA

Position Type:

Full-Time, Salary Exempt

Annual Salary:

$113,000 - $140,000

Overview

:

The Senior Director of Permanent Supportive Housing (SDPSH) is responsible for leading and managing all aspects of Heading Home's Permanent and Transitional Housing programs as well as the Career and Financial Services (CFS) program in collaboration with Senior Director of Emergency Shelter. This includes overseeing service delivery, staffing, and operational effectiveness to ensure program participants receive comprehensive, person-centered support. Reporting to the Vice President of Programs and working in close coordination with program directors and the Senior Director of Real Estate and Facilities, the SDPSH ensures that residents have access to the resources and interventions needed to exit homelessness, stabilize in permanent housing, and make progress toward long-term personal and health-related goals.

Responsibilities / Essential Job Functions

:

General and Leadership

• Develop and implement the strategic vision for Permanent Supportive Housing (PSH) programs in alignment with organizational goals and best practices.
• Oversee the planning, development, and execution of housing and support services to ensure quality, effectiveness, and sustainability.
• Lead, mentor, and manage multidisciplinary teams including program managers and case managers.
• Foster a culture of accountability, collaboration, and continuous improvement across all PSH/CFS teams.

Operational Management and Compliance

• Ensure compliance with local, state, and federal regulations as well as funding requirements and housing quality standards.
• Monitor program metrics, budgets, and contracts to ensure effective resource utilization and outcome achievement.

Program Development & Innovation

• Utilize data-driven approaches to improve service delivery and evaluate program impact.
• Champion a Housing First and trauma-informed approach to support residents in achieving stability, independence, and improved quality of life.
• Ensure culturally competent, equitable, and person-centered services are consistently delivered.

Cross Departmental Collaboration

• Work in close partnership with the Real Estate and Finance teams to address client housing issues, including lease recertifications, landlord concerns, rent arrears, evictions, and other tenancy-related matters to promote long-term housing stability as well as financial stability of the division.

Qualifications / Requirements

:

• Bachelor's degree in Social Work, Public Administration, Human Services, or a related field required; Master's degree strongly preferred.
• Minimum of 7–10 years of progressively responsible experience in housing, homelessness services, or human services, including 5+ years in a senior leadership or program management role.
• Strong understanding or ability to quickly gain a strong understanding of Permanent Supportive Housing, Housing First principles, trauma-informed care, and harm reduction.
• Demonstrated experience supervising multidisciplinary teams.
• Proven ability to manage complex programs, including budgeting, compliance, contracts, and outcomes evaluation.
• Experience working with HUD, local housing authorities, and other government and philanthropic funders preferred.
• Knowledge of landlord/tenant law, eviction prevention strategies, and supportive housing operations.
• Excellent communication, problem-solving, and crisis management skills.
• Demonstrated ability to work collaboratively across departments, especially with real estate, facilities, and property management teams.
• Proficiency with case management systems, data reporting tools, and Microsoft Office Suite.
• Commitment to racial and social equity and experience leading initiatives that promote diversity, equity, and inclusion.

Equal Employment Opportunity Statement

Heading Home, Inc. is an Equal Employment Opportunity (EEO) employer and welcomes all qualified applicants. Applicants will receive fair and impartial consideration without regard to race, sex, color, national origin, age, disability, veteran status, genetic data, gender identity, sexual orientation, religion or other legally protected status, or any other classification protected by federal, state, or local law.

Work Environment

(should include noise level, physical demands such as bending, sitting, lifting) Example: Office space within office building; prolonged sitting at a desk and working on a computer, OR, requires equal amounts of sitting and standing, must be able to climb stairs.

Office is open to the public and visitors only by appointment. Position requires a minimum of four days onsite. Office is climate controlled with heat and air conditioning.