Associate Executive Director
Job Details
Main Building - Portland, OR
Full Time
$107,000.00 - $125,000.00 Salary/year

Associate Executive Director

Outside In is looking for a collaborative, flexible, and entrepreneurial leader to be our Associate Executive Director. The Associate Executive Director will articulate and operationalize our strategic vision for building Outside Ins programs and infrastructure. With oversight of Behavioral Health, Health Services, Youth Services, Support Services, and Quality and responsibility for a $14 million budget, the Director will initially manage a team of 100 including four direct reports.

Outside In is a Federally Qualified Health Center, a licensed mental health and substance use provider, and a founding member of the Homeless Youth Continuum serving patients and clients in the Portland Metro Region. Since 1968, Outside In has transformed thousands of lives by helping break the cycles of chronic homelessness, poverty, and poor health among Portlands LGBTQIA+ community, people of color, those experiencing homelessness, migrants, and the underserved. Our health clinics and young adult programs strive to meet people where they are and provide safe, affirming spaces for our community to receive judgment-free care and support.

The majority of our clients are housing insecure and many experience unsheltered homelessness. We work with individuals who have often struggled to be served well in more traditional clinical treatment settings. Our model uplifts the dignity and beauty of humankind and allows for long-term relationships and flexibility in supporting clients to meet their goals. We believe that nurturing a strong community is critical to the provision of equitable and anti-racist services. We adopt a team approach and collaborate across discipline to support our clients. The impacts of the COVID 19 pandemic, climate change, and systems of oppression weigh disproportionately on the communities we serve. While this position involves sitting with people through significant pain and loss, we also witness an unbelievable amount of strength, resiliency, and beauty.

In this newly created position, the Associate Executive Director will report to and partner with the Executive Director to lead Outside Ins growth and advance its mission. This is an extraordinary opportunity for a purpose-driven leader and creative builder to scale up a transformative organization working to improve our communitys health and wellness. The Associate Executive Director will lead by example and build structures that support the organizations evolution. They will collaborate with and complement the Executive Director to ensure that Outside In continues to be an innovative leader in integrated primary care, behavioral health, harm reduction, and social services.

This is a full-time, exempt position with a starting annual salary range of $107,000-125,000 depending on experience. Outside In offers an excellent benefits package, including employer paid comprehensive medical and dental insurance and short-term and long-term disability insurance. We also offer an Employee Assistance Program; health, dependent care, and transportation flex plans; 403(b) retirement plan with employer contribution and full vestment on day one; 18 days of paid vacation in your first year with increases every year until your sixth year; paid holidays; and an Employee Discount Program that offers employer discounts on everything from dining to cars.

Who you are:

  • You are adaptable, collaborative, and a visionary leader who is energized working in a rapid growth, fast-paced environment.
  • You have the vision and skills to lead teams to plan and implement sustainable growth.
  • You uphold Outside Ins pillars of compassion, courage, responsiveness, acceptance, service, and persistence, and support both a results and staff/client centered culture.
  • You approach leadership as a mentor and coach and hold space for transformational change while supporting a nurturing and human-centered culture.
  • You are an outstanding communicator whose self-awareness and empathetic approach are reflected in your interpersonal skills, including your ability to collaborate with diverse stakeholders.
  • You provide strong, collaborative, and intentional day-to-day leadership to bridge teams and support a results and wellness-driven culture.
  • You apply an intersectional, anti-oppressive, and anti-racist framework that ensures all work lifts and centers BIPOC, non-binary, and LGBTQ+ staff, clients and patients. You are committed to social justice frameworks including race, gender, economic justice, and equity.
  • You are passionate about building a diverse and inclusive culture on a foundation of transparency, open communication, and collaboration.
  • You center authentic engagement with clients and patients to continuously improve and deepen our work and mission.


What you will do:

Strategic Planning and Goal Setting

  • Actively participate in establishing and implementing the overall strategy, business and operation planning, and development growth for the operational programs.
  • Research and assess development strategies, programs and initiatives regarding potential new services for additional growth.


  • With the Executive Director and the SMT, develop annual operating plans and budgets, including staffing and other operating resources to achieve projected goals.
  • With departments and Directors, develop transformational strategies and guide staff in the implementation and execution of process improvement tools and methods.
  • Implement and monitor actions and plans to achieve the operating goals, objectives, policies, procedures, and mission of Outside In.
  • Support Directors in overseeing the day-to-day operations of Health Services, Behavioral Health, Youth Services, Facilities, IT, and Quality Improvement.
  • With Directors, ensure that clinical services are safe, integrated, coordinated, and of high-quality.

Quality Improvement

  • Oversee the QI/QA Plan. Participate in quality initiatives and in the QA committee of the Board.
  • Seek and evaluate data to address clinical and operational needs and use it to implement process improvement.
  • Report quality outcomes to the board.

Financial Management

  • Assist with development, implementation, and monitoring of the annual operating department budgets.
  • Ensure that all revenue and expense budgets and goals are met each year.
  • Work with Finance Director to develop the annual and long-range capital plan.
  • Assist in writing grants to obtain funding from Federal, State and Private Organizations.


  • Assures program and corporate compliance with Federal and State laws, Outside In policies and procedures, and with external regulatory bodies and professional review and licensing boards.
  • Accountable for the development and administration of internal policies and procedures.
  • Assist in the review and remediation of compliance issues in collaboration with the Compliance Manager.

Staff Management

  • Lead and manage staff as assigned through recruitment, retention, mentoring, coaching, and supervision ensuring staff engagement to meet operational and clinical goals and objectives.
  • Support staff development through regular meetings, performance appraisals, initiation of improvement work plans, and personnel actions.
  • Lead staff in team building and strategies to facilitate integration of services.
  • Coach Directors, Managers, and Supervisors in their growth as managers and leaders.
  • Foster an organizational culture that welcomes people in all their diversity, including race, ethnicity, culture, sexual orientation, gender identity/expression, and socioeconomic background.
  • Assure appropriate staffing to deliver quality programs and services.
  • Balance internal (team) community building with accountability for results.
  • Support teams through crisis response.
  • With management, create an agency-wide culture based on equity, anti-racism, that encourages service excellence and achieves outstanding results in patient, client, and staff satisfaction.

Associate Director

  • Acting Executive Director in the absence of the Executive Director.
  • Keep Executive Director informed of issues that jeopardize the achievement of agency goals.


We are committed to having an applicant pool for this position that reflects the diversity of the people we serve, and we highly encourage Black, Indigenous and People of Color and Queer folx to apply.

Studies have shown that women and Black, Indigenous and People of Color are less likely to apply for jobs unless they believe they meet every one of the qualifications as described in a job description. We know that the best candidates for this job might include individuals who havent engaged in traditional educational systems, and if this position speaks to you, we encourage you to apply, even if you don't believe you meet every one of our described qualifications.



  • At least five years progressive operational leadership experience in an integrated health and social services agency/system. Demonstrated leadership, management, financial analysis and planning skills.
  • Superior management skills including a demonstrated ability to build and lead a growing team.
  • Coaching and mentoring skills, including prior experience with staff who work with youth.
  • Creative problem-solving skills, including negotiation and conflict resolution skills.
  • Demonstrated understanding of current healthcare, behavioral health, and social service trends, best practices, and policy issues.
  • Demonstrated understanding of continuum of care for populations experiencing homelessness.
  • Experience, ideally both lived and professional, addressing homelessness.
  • Demonstrated systems thinking experience and proven ability to catalyze effective change through a holistic approach to analysis of systems and structures.
  • Proof of COVID-19 vaccination status or approved medical or religious exception on file is required.

Desired but not required:

  • Prior experience in a Federally Qualified Health Center (FQHC).
  • Prior experience with government grants.
  • Experience in a union environment.
  • Familiarity with managed care contracts and value-based payment.
  • Masters Degree in Health Care Management, business, public health or health care related discipline.


This position is in a typical office and clinic environment, with moderate noise. Both in office and remote work is expected.

This job requires operating phones, computers and other office equipment. Communicating is required on a regular basis. Moving inside the building to other offices and program delivery spaces as well as moving to surrounding sites is expected. Sporadically moves boxes weighing up to 10 pounds.

Application Instructions

Please follow the link of the position for which you wish to apply and complete the online application. A resume and cover letter are requested. You can submit these documents in any format, but pdf works best. In your cover letter, please address the following:

  • How would this position contribute to the pursuit of your long-term professional goals?
  • If you were selected for this position, how would you use your skills and experience to contribute to equity, inclusion and community growth at Outside In?

Applications will be considered as they are submitted so you are encouraged to apply early. Applications will continue to be accepted until the position is filled.