Director of Operations

Cultivate Initiatives; Portland (OR); On-site; USD 82,000 - 88,000; Full time

Job summary

Cultivate Initiatives, based in Portland, OR, seeks a Director of Operations to serve as the senior operations leader, translating strategy into effective day-to-day management across workforce development, housing, and supportive sheltering. You will align resources, set goals and metrics, and foster accountability while guiding teams through growth and change.

In this hands-on role, you’ll partner with the Executive Director and Finance Director to ensure financial sustainability, program

Qualifications

• Significant leadership experience across programs, operations, or multiple functional areas.
• Strategic and tactical thinking with focus on long-term sustainability and organizational growth.
• Strong financial acumen and ability to understand and analyze financial impact of decisions.
• Ability to establish and manage meaningful metrics and translate strategy into measurable results.
• Proven ability to identify root causes of problems and lead through change.
• Highly effective communicator with strong collaboration and judgment.
• Commitment to equity and inclusion in a diverse workplace.

Responsibilities

• Executive Leadership & Strategic Planning: Develop and implement organizational strategy, priorities, and operating plans; translate strategy into goals and metrics.
• Program & Operational Oversight: Lead Directors, ensure performance, quality, and alignment with strategy; monitor funding and deliverables.
• Organizational Management: Foster collaboration, accountability, and inclusive culture; support hiring, development, and retention.
• Financial Stewardship: Develop budgets with finance, ensure sustainable resource use and growth; diversify revenue streams.
• Facilities & Site Operations: Oversee facilities, safety, and day-to-day operations; address maintenance needs.
• External Leadership & Representation: Build relationships with external partners and advocate for CI.
• Board Relations & Communication: Communicate metrics to the Board and participate in committees.

Skills

Leadership

Strategic thinking

Financial acumen

Metrics & measurement

Problem solving

Communication

Equity & inclusion

Job description

About Cultivate Initiatives:

Cultivate Initiatives is a group of people who work alongside those on the margins to empower individuals and communities through an inclusive range of initiatives and support. We build communities from the inside out through workforce development, housing and homemaking, and supportive sheltering.

Cultivate Initiatives values diversity, professional growth, teamwork, and an equitable and inclusive workplace. Employees are expected to apply a lens of equity and inclusion in planning and directing their work and to contribute to a multicultural approach to support a culture of Cherished Belonging.

Position Summary:

The Director of Operations is a key member of Cultivate Initiatives’ executive leadership and serves as the organization’s senior operational leader. Reporting to the Executive Director, the Director of Operations provides leadership for the organization’s three program areas—Workforce Development, Housing & Homemaking, and Supportive Sheltering—as well as facilities.

The Director of Operations works closely with the Executive Director and Director of Finance to translate organizational strategy into effective operations, strengthen performance and sustainability, and align resources with organizational priorities. The Director of Operations establishes clear goals and meaningful metrics, fosters accountability and collaboration, and drives continuous improvement across the organization.

At the heart of the role is ensuring that Cultivate Initiatives has the people, resources, and infrastructure needed to effectively serve people and communities on the margins. This is a hands-on leadership role requiring both strategic perspective and a willingness to step into the work, solve problems, and lead through challenges and change. The Director of Operations provides executive leadership for the organization when the Executive Director is unavailable.

Compensation/Benefits:

• $82,000-88,000 annually depending on experience
• Comprehensive benefits package including health, dental and retirement plans.
• Opportunity to make a meaningful impact by contributing to the success of a non-profit organization.
• Collaborative and inclusive work environment that values diversity and professional growth.

Primary Duties:

Executive Leadership & Strategic Planning

• Partner with the Executive Director and director team to develop and implement organizational strategy, priorities, and operating plans.
• Translate strategy into clear goals, metrics, accountability, and execution across programs and operations.
• Keep the organization’s mission and the needs of the people it serves at the center of operational and strategic decision‑making.
• Identify organizational challenges and opportunities and develop creative, sustainable solutions.

Program & Operational Oversight

• Provide leadership and oversight to the Directors of Workforce Development, Housing & Homemaking, and Supportive Sheltering, ensuring strong performance, quality, accountability, and alignment with organizational strategy.
• Monitor program funding, deliverables, and performance, ensuring commitments are met and programs remain aligned with organizational and contractual requirements.
• Lead continuous improvement and strengthen coordination across programs and operations.
• Ensure programs have the operational support, resources, and infrastructure needed to effectively serve participants and communities.

Organizational Management

• Build a consistent culture across the organization that fosters collaboration, accountability, communication, and inclusion.
• Coach and support directors in achieving organizational goals, developing their teams, and building strong, accountable, collaborative functions.
• Work with Human Resources and organizational leadership to support effective hiring, development, performance management, and retention.

Financial Stewardship

• Partner with the Director of Finance and program directors to develop and monitor budgets and ensure effective use of organizational resources.
• Ensure financial sustainability through understanding the financial impact of operational and programmatic decisions.
• Identify opportunities to strengthen efficiency, resource allocation, and sustainable growth, including through diversifying revenue streams.

Facilities & Site Operations

• Provide oversight of Cultivate Initiatives’ facilities and site operations, including the organization’s building and on-site village.
• Ensure the safety, security, functionality, and effective day-to-day operation of organizational facilities and grounds.
• Partner with staff and external vendors as needed to address facility maintenance, repairs, improvements, and other site-related needs.

External Leadership & Representation

• Represent Cultivate Initiatives with community, governmental, private, nonprofit, and other external organizations as appropriate.
• Build relationships that strengthen the organization’s programs, partnerships, and community impact.
• Provide effective organizational representation and leadership when the Executive Director is unavailable.

Board Relations and Communication

• Establish and maintain regular and clear communications with Board members on operational and program issues.
• Attend board meetings and report on operational and program metrics.
• Lead and/or participate in board and staff committees to advance the mission.

Preferred Competencies, Skills, & Experience:

• Significant leadership experience, including leadership of programs, operations, or multiple functional areas.
• Demonstrated ability to think both strategically and tactically, with an emphasis on long‑term sustainability and organizational growth.
• Strong financial acumen and ability to understand and analyze the financial impact of organizational decisions.
• Demonstrated ability to establish and manage meaningful metrics, use data to assess performance, and translate strategy into measurable results.
• Proven ability to identify root causes of systemic problems, develop creative solutions, and effectively lead through change and complex situations.
• Highly effective communicator and collaborator with strong judgment, emotional intelligence, and the ability to build trust and accountability across an organization.
• Commitment to equity and inclusion, with the ability to lead effectively in a diverse, multicultural workplace.

Work Conditions and Physical Requirements:

• Work is performed indoors.
• Ability to work in environments with varying noise levels, from quiet offices to louder, industrial settings.
• Work requires the ability to perform repetitive movements of the wrist, hands, or fingers due to continuous use of computer keyboards and other office equipment.
• Being physically present in the CI offices from 8:30am – 4:30pm, Monday - Friday
• Must be able to provide proof of Driver’s License

The position is open until filled. Applications received by October 1, will receive priority consideration. If a suitable candidate is found during that screening, later applications will not be considered. We look forward to speaking with you!

CI is committed to maintaining a safe and secure work environment for employees and neighbors. As part of our hiring process, we conduct criminal history checks for the top candidates of all recruitments and driving history checks for candidates of positions that require operating company vehicles. CI also conducts [routine] [episodic] drug tests.

CI is an Equal Opportunity Employer. values a diverse, inclusive workforce and provides equal employment opportunity for all applicants and employees. All qualified applicants for employment will be considered without regard to an individual’s race, color, sex, gender identity, gender expression, religion, age, national origin or ancestry, citizenship, physical or mental disability, medical condition, marital status, domestic partner status, sexual orientation, genetic information, military or veteran status, vaccination status, or any other basis protected by federal, state, or local laws. If you require accommodation to apply, please contact Emily Hutsell at the following number or email.

Questions: [e-mail] or [phone]