Job Description

Boston, MA

Onsite

Position Overview

This organization is redefining how homelessness is addressed—by combining stable housing with the supportive services people need to build lasting independence. Through a thoughtful, trauma-informed approach, they help both individuals and families transition from crisis to self-sufficiency, offering life skills, job training, and financial coaching along the way. With a remarkable 90%+ housing retention rate over the past 18 years, their housing-plus-services model is a proven success. If you're passionate about transformative, people-centered work that truly changes lives, this is a place where your efforts will matter—every single day.

As Senior Director of Permanent Supportive Housing, you will lead the organization’s Permanent and Transitional Housing programs and the Career and Financial Services program, in partnership with the Senior Director of Emergency Shelter. Reporting to the Chief Operating Officer, you will oversee service delivery, staffing, and operations to ensure residents receive person-centered support, exit homelessness, and achieve long-term housing stability and personal goals.

Responsibilities

• Shape and execute the strategic vision for Permanent Supportive Housing (PSH) programs in alignment with organizational priorities and industry best practices
• Direct the planning, development, and delivery of housing and supportive services to ensure quality, effectiveness, and long-term sustainability
• Lead, mentor, and support multidisciplinary teams, including program managers and case managers
• Promote a culture of accountability, collaboration, and continuous improvement across all PSH and CFS programs
• Ensure full compliance with federal, state, and local regulations, funding requirements, and housing quality standards
• Oversee program performance, budgets, and contracts to maximize resources and achieve desired outcomes
• Apply data-driven strategies to strengthen service delivery and measure program impact
• Champion Housing First and trauma-informed approaches to help residents achieve stability, independence, and improved quality of life
• Guarantee delivery of culturally competent, equitable, and person-centered services
• Collaborate with Real Estate and Finance teams to resolve tenancy issues—including lease recertifications, landlord relations, rent arrears, and evictions—while safeguarding both client housing stability and the division’s financial health

Qualifications

• Bachelor’s degree in Social Work, Public Administration, Human Services, or related field required; Master’s degree strongly preferred
• 7+ years of progressive experience in housing, homelessness services, or human services, including 5+ years in senior leadership or program management
• Deep knowledge—or ability to quickly develop expertise—in Permanent Supportive Housing, Housing First, trauma-informed care, and harm reduction
• Track record of supervising, mentoring, and supporting multidisciplinary teams
• Skilled in overseeing complex programs, with experience in budgeting, compliance, contract management, and outcomes evaluation
• Familiarity with HUD, local housing authorities, and other public or philanthropic funders preferred
• Understanding of landlord/tenant law, eviction prevention, and supportive housing operations.
• Strong communication, problem-solving, and crisis management skills
• Ability to collaborate effectively across departments, particularly with real estate, facilities, and property management teams
• Proficient in case management systems, data reporting, and Microsoft Office Suite
• Demonstrated commitment to racial and social equity, with experience advancing diversity, equity, and inclusion initiatives

Compensation

• Salary: $113,000 – 134,000
• Medical, Dental, and Vision insurance
• Pet insurance
• Life and Disability Insurance
• Commuter benefit program
• 9 paid holidays, 20 days of PTO, 12 sick days
• Employer-sponsored retirement program

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