Deputy Director of Administration

The Pathfinder Network•Portland, OR

1d•Onsite

About The Position

The Deputy Director of Administration is a senior strategic leader responsible for the vision, effectiveness, and long-term direction of The Pathfinder Network's organizational support team, including Operations, Finance, and People & Culture. This role partners with the Executive Director, Senior Leadership Team, and Leadership Team to strengthen the systems, resources, culture, and organizational capacity needed to achieve the agency's mission, vision, values, and strategic priorities. The Deputy Director leads through Directors and other agency leaders, creating clarity, accountability, and collaboration across functions while ensuring infrastructure is integrated, responsive, compliant, and positioned for sustainable growth. This position carries primary accountability for the administrative health of the agency, exercising delegated authority during the Executive Director's absence. The role involves leading by example, modeling and driving a culture of accountability and support, and shaping a workplace where people feel valued, supported, and inspired to do their best work. This position supervises the Organizational Support Team leadership, currently including the Director of Finance, Director of Operations, and Director of People & Culture. The Deputy Directors jointly support cross-organizational alignment, leadership effectiveness, delivery of agency strategy, and organizational success and sustainability while maintaining primary accountability for their respective portfolios. The Pathfinder Network is seeking an inspirational, inclusive, and relational leader who can deliver with excellence and help grow the agency and its impact serving justice-involved individuals, families, and communities.

Requirements

Master's degree in business administration, nonprofit management, organizational leadership, or a related field, or an equivalent combination of education and significant relevant leadership experience.
Six or more years of progressively responsible organizational, administrative, operational, financial, people, or nonprofit leadership experience.
Six or more years of experience supervising a diverse team, including experience supervising and developing Director- and Manager-level leaders.
Experience leading multiple departments or functional areas and implementing strategic initiatives from planning through implementation.
Experience providing strategic oversight of finance, operations, people-related functions, organizational systems, or a combination of these areas.
Experience with organizational planning, change management, process improvement, risk management, or organizational development.
Experience working in nonprofit organizations and providing organizational leadership as part of an Executive or Senior Leadership Team.
Experience partnering with a Board of Directors, including preparing and presenting materials to a board or board committee.
Fluency with the systems a senior leader relies on to run an organization: financial and accounting systems, HRIS and payroll, case management or client data systems, board and project reporting tools, and the data analysis needed to interpret them.
Ability to work independently with limited supervision while managing highly strategic, mission-critical work and priorities.
Lived experience with the criminal legal system, incarceration, community supervision, and/or addiction and recovery is valued and strongly preferred, and is considered a meaningful qualification for this role alongside professional experience.
Must possess a valid driver’s license and have access to a motor vehicle during work hours that is covered by adequate car insurance.
Must complete a background check, employment verification, motor vehicle records check, and a drug screen that does not test for marijuana.
Commitment to racial justice: Staff are expected to interact effectively across racially diverse teams, partners, and experiences, apply a racial equity lens in their work and commit to the ongoing work required to move TPN toward a more diverse, equitable, and inclusive and just organization.

Nice To Haves

Lived experience with the criminal legal system, incarceration, community supervision, and/or addiction and recovery is valued and strongly preferred, and is considered a meaningful qualification for this role alongside professional experience.

Responsibilities

Drive the vision, strategy, and long-term priorities for the Organizational Support Team, ensuring alignment with the agency’s mission, vision, values, and strategic plan.
Partner with the Executive Director and Senior Leadership Team to translate organizational priorities into clear administrative, financial, operational, and workforce goals.
Anticipate organizational needs and strengthen the capacity, structures, systems, and resources necessary to achieve the agency’s current and future priorities.
Serve as a senior leader in organizational effectiveness, readiness, sustainability, and the continuous development of TPN's internal infrastructure.
Lead Organizational Support functional team and participate in Functional Lead meetings to lead and drive agency strategic priorities.
Co-lead Leadership Team meetings alongside the Deputy Director of Programs and help ensure coordinated effort across the agency.
Represent the Executive Director in internal and external forums when delegated and speak for the agency's administrative and operational commitments.
Serve as the Executive Director's principal thought partner and confidential advisor.
Provide strategic leadership and oversight of Operations, Finance, and People & Culture, ensuring these functions are aligned, integrated, and positioned to support the agency’s mission.
Strengthen organizational infrastructure, systems, and processes to promote effectiveness, sustainability, innovation, and continuous improvement.
Ensure Directors have clear accountability for functional strategy, day-to-day management, performance, staffing, and results within their areas of responsibility.
Promote and ensure intra and interdepartmental collaboration, systems integration, and coordinated solution generation to ensure delivery of functional department and agency goals.
Identify cross-functional gaps, duplication, or inefficiencies and lead improvements that make organizational systems easier to navigate, more responsive, and more effective.
Partner with the Director of Finance and Executive Director to align financial planning, resource allocation, and organizational priorities.
Ensure financial strategy, forecasting, daily operations, and decision-making support organizational sustainability, growth, and mission impact.
Provide strategic oversight of organizational risk, compliance, internal controls, administrative policies, and operational readiness in partnership with functional Directors and the Executive Director.
Ensure Operations systems and infrastructure effectively support staff, programs, facilities, technology, safety, continuity, and changing organizational needs.
Use organizational and financial data to identify risks, trends, capacity needs, and opportunities for greater efficiency and effectiveness, and ensure appropriate mitigation or improvement plans are implemented.
Hold and protect confidential information with consistent discretion.
Ensure the Executive Director is briefed and decision-ready: surface emerging risks and opportunities early and directly.
Provide strategic leadership and oversight of workforce planning, organizational development, and employee experience in partnership with the Director of People & Culture.
Promote a culture of accountability, collaboration, empowerment, and belonging that supports employee and organizational success.
Develop and sustain leadership capacity and continuity, organizational readiness, and a strong internal talent bench to support continuity and future growth including intentional development pathways for staff with lived experience.
Provide strategic direction for employee and leadership learning and development, ensuring workforce development priorities build capacity and align with organizational goals.
Ensure people systems, policies, and practices are aligned with organizational values, equity commitments, legal requirements, and the agency's approach to shared leadership.
Provide leadership, direction, and support to Directors within the Organizational Support Team.
Directly supervise, develop, and evaluate Director-level staff, providing coaching, feedback, and support to strengthen leadership effectiveness.
Support Directors in navigating complex organizational challenges, decision-making, and cross-functional priorities.
Work to create and maintain a workforce reflective and responsive to the communities we serve.
Prioritize lived experience and help sustain an agency culture that supports a diverse, representative, and stable workforce.
Champion a culture of wellness, regulation, relational leadership, and accountability, including the agency's Creating Regulation and Resilience communication model.
Examine, develop, implement, document, and communicate the goals, priorities, and values of the agency.
Provide strategic and visionary leadership for the agency in partnership with the Leadership Team.
Prepare for, attend, and participate in leadership meetings and other meetings to work towards fulfilling agency mission, vision and values.
Lead and serve on initiatives, temporary teams and work groups.
Collaborate with agency staff and stakeholders to carry out the mission of TPN.
Represent the agency positively and build relationships with stakeholders and the communities we serve.
Model and drive a culture of accountability and support, in alignment with the Two Accountabilities.
Support agency growth and sustainability and model the values and mission of TPN.
Serve as the Executive Director's designated backup when delegated, supporting continuity of leadership and decision-making during periods of absence.
Maintain a working knowledge of the agency's programs sufficient to speak credibly about TPN's participants, programs, and outcomes.
Be a champion in the shaping and sustaining of a diverse, equitable, inclusive and just workplace, with a focus towards creating racial equity.
Participate on cross-departmental teams or committees regarding organizational policies, processes and work environment.
Participate in Temporary Teams, Equity Team, Employee Resource Groups, and other teams.
Contribute individualized skills, knowledge, experience, and expertise to help the agency reach its mission.

Benefits

Generous paid time off (12 accrued vacation days + 12 accrued sick days during your first year of employment, mental wellness hours)
17 paid days of significance each year
Extended holiday days of significance with a week off at the end of the year and 3 4-day weekends
Paid 30-minute lunch breaks
Employer-paid employee-only medical, vision and dental coverage starting first day of employment
Flexible Spending Account
Dependent Care Assistance Program
Employer-funded Lifestyle Spending Account
401k retirement plan with 3% employer match, fully vested immediately
Employer-paid short-term disability and accidental death and dismemberment
Supplemental virtual healthcare for employees and dependents
Eligibility for Public Service Student Loan forgiveness
Employee recognition program, staff appreciation awards and swag store
Bilingual pay differential for eligible positions
Shared Leadership model and opportunities to contribute to agency success and growth
Development opportunities and trainings