Executive Director

Scion Executive Search is proud to partner with Outside In , a longstanding nonprofit organization dedicated to advancing health, dignity, and opportunity for youth and other marginalized communities experiencing barriers to stability and well-being, in the search for its next Executive Director . This is an exceptional opportunity for an experienced, mission-driven executive to lead a respected Portland institution through an important period of organizational renewal, strengthening its operations, culture, and financial sustainability while preserving its deep commitment to social justice and community impact. The Executive Director will provide strategic, operational, and cultural leadership to a complex, multidisciplinary organization, working closely with the Board of Directors, staff, community partners, and supporters to ensure Outside In remains a trusted and essential resource for the communities it serves. This is a full-time, onsite opportunity based in Portland, Oregon. Local candidates are preferred; however, highly qualified candidates seeking relocation are encouraged to apply. ABOUT THE ORGANIZATION: For nearly six decades, Outside In has worked to transform lives by helping youth experiencing homelessness and other marginalized people access essential healthcare, supportive services, and opportunities to achieve greater stability and independence. Rooted in a commitment to social justice, equity, and harm reduction, the organization serves individuals who have historically faced significant barriers to care, housing, and community resources. Through an integrated network of programs spanning primary healthcare, behavioral health, substance use services, youth support, education and job training, housing-related services, and other community-based initiatives, Outside In serves more than 10,000 individuals annually across the Portland region. With approximately 200 employees, multiple service locations, and an annual operating budget of approximately $26 million, Outside In combines the reach and complexity of a healthcare organization with the deeply personal, relationship-centered approach of a community-based nonprofit. As Outside In enters its next chapter, the organization seeks a thoughtful, experienced leader who can honor its legacy, strengthen organizational resilience, and build a shared vision for a sustainable future. POSITION OVERVIEW: Reporting to the Board of Directors, the Executive Director will serve as Outside In's chief executive, responsible for organizational strategy, financial stewardship, operational effectiveness, external relationships, and the overall health of its workplace culture. The incoming leader will join an organization with a deeply committed team, a powerful mission, and significant opportunities to adapt an operating model to be more sustainable in the current environment. Success will require a leader who combines sound business judgment with genuine compassion, emotional intelligence, and an unwavering commitment to the communities Outside In serves. The Executive Director must be equally comfortable navigating complex financial and operational decisions, engaging thoughtfully with passionate staff and stakeholders, and representing the organization as a trusted community leader. Above all, Outside In seeks an executive who understands that organizational strength and mission impact are interconnected, and who can bring people together around a clear, achievable path forward. RESPONSIBILITIES: Partner with the Board of Directors and senior leadership to establish a clear strategic vision that advances Outside In's mission while strengthening organizational stability and long-term sustainability. Provide executive oversight of financial strategy, budgeting, and operations, ensuring responsible resource management, regulatory compliance, and sustainable service delivery. Evaluate programs, funding models, and operational systems to improve efficiency, strengthen financial performance, and maximize community impact. Guide organizational change with transparency and accountability, fostering a collaborative, inclusive workplace culture grounded in trust, open communication, and shared commitment to the mission. Develop and empower a high-performing senior leadership team while strengthening relationships with employees, labor representatives, and stakeholders throughout the organization. Serve as a trusted strategic partner to the Board of Directors, supporting effective governance, transparent communication, and risk-informed decision-making. Act as a visible and credible ambassador for Outside In, cultivating relationships with donors, government agencies, healthcare partners, and community stakeholders. Partner with development leadership and the Board to strengthen fundraising efforts, diversify revenue streams, and advance strategic partnerships that support long-term organizational impact. REQUIREMENTS: Significant senior-level leadership experience within a nonprofit, healthcare, human services, youth services, or similarly complex organization, with demonstrated success leading multidisciplinary teams and advancing organizational strategy. Proven ability to provide strategic direction, oversee complex operations, and guide organizations through periods of change, growth, or transformation. Understanding of healthcare delivery, community-based services, and associated regulatory and funding environments. Experience with Federally Qualified Health Centers (FQHCs), HRSA compliance, Medicaid reimbursement, or integrated care models is highly valued. Strong financial acumen, including experience managing substantial budgets, navigating funding challenges, improving operational effectiveness, and ensuring long-term organizational sustainability. Demonstrated success building, developing, and empowering high-performing leadership teams while fostering a collaborative, transparent, and accountable workplace culture. Proven experience