Executive Director

Executive Director
Outside In | Portland, Oregon

About Outside In
Outside In is a dynamic, mission-driven Federally Qualified Health Center (FQHC) dedicated to serving houseless youth and marginalized communities in Portland, Oregon. With over 50 years of impact, we provide critical healthcare, housing, and support services to empower individuals on their path to stability and self-sufficiency. As a unionized nonprofit, we are committed to social justice and innovative solutions that address systemic barriers.

The Opportunity
Outside In is seeking a strategic, financially savvy, and courageous Executive Director (ED) to lead our organization into its next chapter. Reporting to the Board of Directors, the ED will drive strategic planning, financial sustainability, program excellence, and advocacy efforts while fostering an inclusive and high-performing culture. This is a rare opportunity for a visionary yet pragmatic leader to make a lasting impact in the lives of Portland’s most vulnerable populations.

Key Leadership Priorities

• Strategic Decision-Making & Vision: Lead with clarity, balancing organizational growth with operational excellence. Ensure long-term sustainability while adapting to evolving community needs.
• Financial & Operational Leadership: Provide fiscal oversight, drive financial sustainability, and ensure compliance with FQHC and funder requirements.
• Organizational Change Management: Strengthen accountability at all levels, implement systems improvements, and support a culture of transparency and innovation.
• Strong & Decisive Leadership: Navigate complex challenges with confidence, making timely and strategic decisions without undue influence from external pressures.
• Staff & Board Engagement: Inspire and mentor a talented leadership team while collaborating closely with the Board of Directors to advance Outside In’s mission.
• Public & Community Relations: Serve as the face of the organization, engaging with donors, government agencies, community partners, and policymakers to enhance our impact.

Key Qualifications

• At least 10 years of successful and progressively growing responsibility in healthcare leadership, including 3+ years at the executive level.
• Strong financial and business acumen, with a track record of fiscal stewardship in complex organizations.
• Exceptional communication and interpersonal skills to build trust across diverse stakeholders.
• Experience in FQHC, FQHC lookalike, healthcare administration, or nonprofits preferred.
• Experience leading unionized teams and working within a labor-management framework.
• A deep understanding of systemic barriers impacting marginalized communities.
• Ability to develop and execute strategic plans, driving measurable impact.
• Proven success in fundraising, government contract negotiation, and resource development.

Why Join Outside In?

• Lead a respected organization with a 50+ year legacy of impact.
• Work with a passionate, mission-driven team dedicated to social justice and serving those most marginalized.
• Engage in high-level advocacy and systems change work.
• Competitive salary and benefits package, including healthcare, retirement, and professional development opportunities.

How to Apply
Interested candidates should visit www.outsidein.org to review and apply to the full job posting and submit their application. Please include a resume and a cover letter detailing your qualifications and leadership philosophy. Applications will be reviewed on a rolling basis.

No 3^rd party recruiters