At Portland Street Medicine, we offer our houseless neighbors accessible whole-person care to improve and support health, and to bridge a gap in trust between people and systems. Powered by a corps of 150 volunteers and a small staff, PSM meets the growing medical and health needs of those experiencing homelessness in Portland. Through regular and ongoing care on the streets of Portland, we strive to engage with our patients – building capacity to navigate the web of services they need to achieve their goals.
Current Openings:
Executive Director
POSITION DESCRIPTION: Executive Director
Organization: Portland Street Medicine
Location: Portland, Oregon
Status: Full-Time, Exempt
Reports To: Board of Directors (via Board Chair)
Position Summary
The Executive Director (ED) is the chief executive of Portland Street Medicine (PSM) and is responsible for the overall strategic, financial, and operational leadership of the organization. The ED ensures that PSM’s mission—bringing healthcare to people experiencing homelessness—is fulfilled through effective programs, sound financial management, thoughtful community engagement, and alignment with nonprofit best practices.
Working in close partnership with the Board of Directors, the ED will provide leadership in strategic planning, staff development, fundraising, operations, compliance, and external relations.
Key Responsibilities
Leadership & Strategy
Uphold and promote the mission, values, and strategic goals of Portland Street Medicine.
Provide visionary leadership in alignment with the strategic plan developed in collaboration with the Board.
Ensure organizational sustainability and mission impact through effective program development and evaluation.
Governance & Board Support
Serve as the primary liaison to the Board of Directors; provide timely and accurate reports, and execute board-approved policies.
Advise the Board on organizational matters, risks, and opportunities to inform governance decisions.
Operations & Organizational Management
Oversee day-to-day operations, ensuring effective infrastructure to support mission delivery, including HR, finance, IT, communications, and compliance.
Supervise and support staff and key volunteers; lead recruitment, hiring, onboarding, and performance evaluations.
Develop, implement, and monitor internal policies and procedures to promote organizational health and accountability.
Financial Management
Prepare and manage the annual budget.
Ensure sound financial controls and reporting practices; monitor monthly cash flow, reconcile income and expenses, and oversee annual financial reviews or audits.
Seek opportunities to diversify funding streams to maintain a strong financial position.
Fundraising & Development
Lead and support the implementation of the annual fundraising strategy.
Cultivate relationships with individual donors, foundations, corporate partners, and government funders.
Oversee grant applications, compliance tracking, and reporting requirements.
Community Engagement & Partnerships
Represent Portland Street Medicine at community forums, coalitions, and stakeholder meetings.
Maintain strong, strategic relationships with partner organizations, government agencies, healthcare systems, funders, and the broader public.
Compliance & Risk Management
Ensure compliance with local, state, and federal nonprofit regulations and laws.
Oversee insurance coverage, licensing, and organizational policies that mitigate risk and ensure safety.
Maintain up-to-date knowledge of nonprofit and healthcare regulations applicable to the organization.
Other Duties
Perform other duties as assigned by the Board of Directors in service of PSM’s mission and sustainability.
Required Qualifications
Bachelor’s degree in a related field; Master’s degree or equivalent experience preferred.
3–5 years of progressively responsible nonprofit and/or healthcare leadership experience.
Demonstrated experience with staff supervision, budget oversight, fundraising, and program management.
Experience working with or within healthcare systems, community health, or homeless services.
Passion for PSM’s mission and commitment to equity, dignity, and community-centered care.
Knowledge, Skills & Abilities
Strong leadership and decision-making skills with a collaborative and transparent management style.
Excellent written and verbal communication skills; able to effectively represent the organization publicly.
Solid understanding of nonprofit finance and budgeting, including restricted funding and grant compliance.
Proficient in Microsoft Office, QuickBooks (or other accounting platforms), and donor databases.
Ability to thrive in a dynamic, community-facing organization where flexibility and innovation are key.
Physical & Environmental Requirements
Ability to remain in a stationary position and/or move throughout the office and community settings.
Ability to occasionally lift or move objects up to 20 pounds.
Prolonged use of computers and other office equipment may be required.
Occasional participation in outdoor or community-based events.
Behavioral Expectations
Demonstrate a positive and respectful attitude with staff, volunteers, clients, and community partners.
Maintain confidentiality and uphold organizational values in all interactions.
Foster a culture of inclusion, empathy, and equity in both internal operations and external relationships.
Compliance
OSHA Statement: PSM is committed to providing a safe and healthy work environment in compliance with OSHA regulations and internal safety standards. Staff are expected to adhere to all safety policies following appropriate training.
Job Type: Full-time
Pay: $110,000.00 - $130,000.00 per year
Benefits:
401(k)
401(k) matching
Dental insurance
Flexible schedule
Health insurance
Paid time off
Vision insurance
Work Location: In person
Peer Supervisor
POSITION DESCRIPTION: Peer Supervisor
Organization: Portland Street Medicine
Location: Portland, Oregon
Status: Non-exempt
Position Type: 0.8 FTE (32 hours/week)
Reports To: Clinical Care Director (primary) or Executive Director
Position Summary
The Peer Supervisor is a new leadership role that combines direct peer service delivery with supervisory responsibilities. Most of the position focuses on resource navigation and client support—coordinating care, facilitating referrals, and supporting outreach teams. A smaller portion of the role involves supervising peer staff, ensuring compliance with Measure 110 Oregon Administrative Rules (OARs), and providing direction, mentorship, and accountability.
Because this is a new role, responsibilities are expected to evolve as the position grows, programs develop, and the needs of the unhoused community shift. The Peer Supervisor may also step in to support Peer Support Specialist duties at community health events or during staff absences.
Key Responsibilities
Direct Service & Care Coordination
Serve as a primary point of contact for client referrals and resource navigation.
Coordinate care by scheduling Street Care Teams and maintaining continuity of care between visits.
Collaborate with interdisciplinary teams to support whole-person care planning.
Maintain timely and accurate documentation in PSM’s EHR, HMIS, and other databases.
Assist with resource preparation, route planning, and communication with outreach teams.
Provide in-person or phone-based support during outreach events, and occasionally accompany clients to appointments.
Participate in on-call rotation (2–3 shifts/month).
Supervision & Team Support
Provide weekly supervision to peer staff in compliance with M110 OARs, with a focus on role integrity and the discipline of peer-delivered services.
Mentor, support, and guide peer staff in their professional development.
Supervisory duties include assigning work, directing priorities, approving schedules, and evaluating performance.
Step in for coverage or backup support during peer staff absences or high-volume times.
Organizational & Program Development
Support program evaluation, quality improvement, and service coordination efforts.
Contribute to the growth and sustainability of peer-delivered services in partnership with leadership.
Participate in team meetings, collaborative planning, and organizational events.
Qualifications
Required
Certification as an Addiction Peer Support Specialist (PSS), Certified Recovery Mentor (CRM), or Addiction Peer Wellness Specialist (PWS).
At least one year of experience as a PSS, CRM, or PWS in substance use disorder and addiction recovery services.
Valid driver’s license and an acceptable driving record.
Preferred
Supervision, mentorship, or leadership experience.
Experience with documentation systems and care/service coordination.
Familiarity with local resource networks for substance use, housing, and healthcare.
Experience providing peer services in outreach, community, or healthcare settings.
Strong understanding of harm reduction, trauma-informed care, and peer role integrity.
Additional Information
Some evening or weekend hours may be required depending on outreach needs.
This role includes a mix of office, community, and field-based work.
Regular driving of organizational vehicles will be required for outreach and community events.
Physical requirements may include lifting up to 30 lbs, walking several miles, and standing for extended periods.
This is a new, grant-funded position, and responsibilities will adapt as the role grows and responds to organizational and community needs.
Job Types: Full-time, Part-time
Pay: $32.00 - $35.00 per hour
Expected hours: 32 per week
Benefits:
403(b)
403(b) matching
Bereavement leave
Dental insurance
Flexible schedule
Health insurance
Paid time off
Professional development assistance
Vision insurance
Work Location: In person
PSM’s BACKGROUND Check Policy
As a medical organization and nonprofit, Portland Street Medicine conducts background checks with the ultimate goal of keeping our patients safe.
As an organization that seeks to incorporate people with lived experiences of homelessness and poverty at every level of our organization, we also recognize that background checks may present a barrier for volunteers and staff with lived experience – and thus, could damage our ability to perform our work in the community. We recognize the criminal justice system is filled with deep inequities, and that homelessness is still criminalized throughout the United States. Background checks, when conducted in a more restrictive way, would restrict those best able to do the work of PSM from being a part of our organization. PSM has a strong “business necessity” to both perform background checks and to welcome volunteers and staff with lived experience who may have criminal records precisely because of those experiences.
For details on our full policy, please follow this link: PSM Background Check Policy