Executive Director

Overview:

Leading Philadelphia's Housing First Pioneer Through Transformational Growth

Pathways to Housing PA seeks an exceptional Executive Director to guide this groundbreaking $25 million organization through a pivotal moment of expansion and leadership transition. This is a rare opportunity to lead an organization that has fundamentally transformed how Philadelphia addresses homelessness, achieving an extraordinary 85% housing retention rate among the more than 550 individuals it serves at any given time.

The Executive Director will join Pathways during an unprecedented period of growth, backed by a transformational multi-year grant from the Pew Charitable Trusts. This leader will partner closely with founding President & CEO Christine Simiriglia while preparing for eventual succession to the top role. The position calls for someone who can build trust, strengthen operations, and expand impact while maintaining an unwavering commitment to the radical compassion at the heart of Housing First.

This role is ideal for a visionary operational leader who understands that ending homelessness requires both business acumen and deep humanity – someone who can navigate government relationships, contracts, and compliance requirements in the morning, then sit with program participants and frontline staff in the afternoon, bringing authentic presence to every interaction.

About the Company:

Since 2008, Pathways to Housing PA has grown from a $2.5 million startup to a $25 million comprehensive service organization, pioneering the Housing First model in Philadelphia. The organization serves individuals experiencing chronic homelessness who have serious mental illness, substance use disorders, and other disabilities, providing immediate access to permanent housing without preconditions of sobriety or treatment compliance.

What sets Pathways apart is not just its housing program, but its holistic ecosystem of services that address every aspect of participants' lives:

Core Programs:

• Housing First Program: The flagship initiative providing scattered-site permanent housing with intensive case management, achieving sector-leading retention rates through unconditional support
• Integrated Care Clinic: Launched in 2015 with Jefferson Health and Project HOME, offering on-site primary care, psychiatry, and behavioral health services with a trauma-informed approach
• Opioid Use Disorder Center of Excellence: A state-funded treatment center serving 225+ participants annually with medication-assisted treatment and recovery coaching
• Philadelphia Furniture Bank: A social enterprise established in 2014 that transforms empty apartments into homes, furnishing 1,400 homes annually for clients from Pathways and 70+ partner agencies
• Good Haul: A 2022 junk-hauling social enterprise that generates revenue while diverting usable items to those in need
• Work First Employment Program: Providing transitional employment and job coaching to 15+ participants, building skills for mainstream workforce re-entry.
• Alumni Association: Ensuring continued community connection for participants who have achieved housing stability
• Housing First University: Spreading the model nationally through training and consulting services

With approximately 140 dedicated staff members, Pathways operates at the intersection of housing, healthcare, and human dignity, proving daily that housing is healthcare and that everyone deserves a home.

Candidate Profile:

The Opportunity and Challenge

The Executive Director inherits an organization with remarkable achievements and its own set of challenges. A recent staff survey revealed the need for authentic, relational leadership to unite the team. Simultaneously, the organization must navigate political uncertainty around government funding (comprising 80% of revenue), implement new quality improvement systems, and develop sustainable growth strategies.

The Pew Charitable Trusts' five-year growth grant provides resources to address these challenges while expanding services. The new Executive Director will lead the implementation of the investment, ensuring Pathways leverages these funds to broaden impact while strengthening internal operations and culture.

This role offers clear succession planning, with a two-year transition period to prepare for assuming the President & CEO position. The successful candidate will have the unique opportunity to learn from a founding leader while bringing fresh perspectives to sustain the mission for decades to come.

The Ideal Candidate

We seek a leader who embodies both operational excellence and radical compassion. The ideal candidate brings proven nonprofit leadership experience, preferably in housing, behavioral health, or social services, with demonstrated ability to manage complex operations while maintaining deep connection to mission and frontline work.

This individual doesn't need direct Housing First experience but must demonstrate unwavering philosophical alignment with harm reduction principles and unconditional support for marginalized populations. They understand that meeting people where they are isn't just a slogan, but a daily practice that requires courage, creativity, and conviction.

The successful candidate thrives in environments that require them to bridge multiple worlds – translating between "social work speak" and "business speak," building trust with both trauma survivors and government officials, and balancing radical compassion with fiscal responsibility. They lead through relationships rather than hierarchy, building consensus while making tough decisions when needed.

Professional Characteristics:

1. Minimum 7 years of leadership experience, preferably in progressive nonprofit organizations serving vulnerable populations, with demonstrated success in senior operational roles
2. Deep philosophical alignment with Housing First and harm reduction principles, with the ability to advocate for these approaches even when controversial
3. Proven track record of building trust and cultivating a healthy organizational culture, particularly in environments that have experienced relationship challenges
4. Excellence in financial management, including experience with government contracts (Medicaid, HUD - preferred) and navigating political uncertainty affecting funding
5. Demonstrated ability to lead through crisis and uncertainty while maintaining team morale and organizational focus
6. Experience with data-driven decision making and accountability systems that improve performance without sacrificing compassion
7. Exceptional emotional intelligence with the ability to authentically engage diverse stakeholders from program participants to policymakers

Key Responsibilities:

The Pathways Leader

• Views housing as a human right, not a reward for compliance
• Builds authentic relationships across all organizational levels
• Balances compassion with accountability
• Thrives in complexity and ambiguity
• Leads through influence rather than authority
• Maintains hope while confronting society's toughest challenges

Strategic Leadership & Organizational Culture

• Partner with the President & CEO to shape organizational strategy while focusing primarily on internal operations and culture transformation
• Lead implementation of the strategic plan, translating vision into measurable action
• Develop and execute business plans leveraging the Pew Charitable Trusts grant for sustainable growth
• Build trust and strengthen relationships across all levels of the organization
• Foster a culture that embodies Housing First values while ensuring operational excellence

Operational Excellence

• Provide inspirational leadership to the senior management team, including Sr. Directors of Housing First Services, Compliance & CQI, and Human Resources, plus the Executive Assistant
• Co-manage VP of Advancement & Social Enterprise and Sr. Director of Finance & Administration with the President & CEO
• Ensure program quality and compliance across all service areas while maintaining person-centered approaches
• Implement data-driven accountability systems that improve outcomes without compromising the mission
• Guide the organization through multiple concurrent challenges, including infrastructure needs and quality improvements

Financial Stewardship & Sustainability

• Oversee $25 million budget with a sophisticated understanding of government contract management
• Navigate political uncertainty affecting 80% government-funded revenue streams
• Develop diversified funding strategies to ensure long-term sustainability
• Monitor financial performance and program outcomes against strategic goals
• Ensure compliance with complex funder requirements while advocating for flexibility to serve participants effectively

Stakeholder Engagement

• Build and maintain trust with internal stakeholders through a visible, authentic presence
• Develop strong relationships with government officials, particularly Medicaid and HUD representatives
• Support the Board of Directors with comprehensive reporting and committee coordination
• Represent Pathways in community forums, policy discussions, and media opportunities
• Bridge diverse stakeholder groups through exceptional code-switching abilities

Succession Leadership

• Learn organizational history and culture from the founding CEO during the two-year transition
• Gradually assume increased external responsibilities while maintaining internal focus
• Prepare for eventual succession to the President & CEO role
• Honor organizational legacy while bringing fresh perspectives for future growth

Core Competencies

Housing First & Harm Reduction Philosophy: Unwavering commitment to unconditional housing and support, with the courage to defend these principles against skepticism and political pressure

Relational Leadership & Trust Building: Authentic presence and genuine care that builds relationships and maintains connection despite organizational growth and complexity

Data-Driven Accountability Management: Ability to implement accountability systems that improve performance while respecting the challenging nature of frontline work

Strategic Financial Management: Sophisticated understanding of government funding streams with the ability to navigate political uncertainty while developing sustainable revenue strategies

Crisis Management & Adaptive Leadership: Proven ability to lead through multiple simultaneous challenges while maintaining team stability and mission focus

Collaborative Decision-Making: Excellence in facilitating shared governance and building consensus while maintaining forward momentum

Emotional Intelligence & Code-Switching: Exceptional ability to authentically engage diverse audiences, from trauma survivors to corporate donors, adapting style while maintaining core values

Organizational Information:

The Executive Director will have several direct reports, as well as co-managing responsibilities for the VP of Advancement & Social Enterprise and the Sr. Director of Finance & Administration with the President & CEO. This leader will partner closely with founding President & CEO Christine Simiriglia while preparing for eventual succession to the top role.

Relevant Financial Information:

Pathways to Housing currently operates on an annual budget of approximately $25 million.

Service Area / Industry Information:

The organization serves individuals in the Philadelphia region experiencing chronic homelessness who have serious mental illness, substance use disorders, and other disabilities, providing immediate access to permanent housing without preconditions of sobriety or treatment compliance.

Notes / Additional Information:

Pathways to Housing PA is deeply committed to equity. We strongly encourage applications from candidates who reflect the communities we serve, including people with lived experience of homelessness, mental health challenges, or substance use recovery. We are an equal opportunity employer and welcome candidates of all backgrounds who share our commitment to housing as a human right.

"This role requires someone exceptional – not just a skilled nonprofit executive, but a leader who can hold multiple truths, bridge different worlds, and maintain hope while dealing with society's most challenging issues."

Email your resume to Monica Wildes, MHS at diverseforce.pthed@comeetapply.com by August 10, 2025, using the subject line: Job Posting Site – Executive Director. This is the final date for applications. Please disregard the dates noted elsewhere on the job site. Confirmation of receipt of the application will be sent by return email. Virtual screening with preferred candidates will be arranged forthwith. Finalists may be asked to a second in-person interview and to complete a brief personality/skills assessment. No phone calls, please.