Worksystems is seeking a dynamic, relationship-focused Executive Director committed to improving the quality of the workforce in the City of Portland and Multnomah and Washington counties. The Executive Director is responsible for strategic, fiscal, and program oversight and overall leadership for the organization. Responsibilities include leading and implementing a comprehensive strategic vision, producing a financially sound budget, developing and maintaining strong relationships and partnerships, managing staff, and supporting effective collaboration throughout the region and state.
The Executive Director provides strategic leadership for the regional workforce system by coordinating and aligning workforce partners to support individual prosperity and advance business competitiveness. Through strong, inclusive partnerships, the Executive Director integrates resources, systems, and community priorities into a cohesive and responsive workforce system. This role builds and sustains high-impact relationships with funders, partners, and community stakeholders, bridging public and private sectors to strengthen collaboration and outcomes. The Executive Director also actively engages with local, regional, state, and national elected officials and public entities to advocate for policies, investments, and strategies that support the region’s economic and workforce development goals.
Reporting to the Board, the Executive Director ensures strong organizational performance by overseeing efficient day-to-day operations, technology, and compliance with all legal and regulatory requirements, while proactively managing risk and maintaining accountability. Through thoughtful, intentional leadership, they collaborate to recruit, lead, mentor, and develop high-performing teams, fostering an inclusive culture supported by policies that promote professional growth, engagement, and retention. Serving as the primary liaison between the board and staff, the Executive Director keeps both informed, aligned, and engaged, and supports board development and recruitment to ensure the board is well-positioned to fulfill its governance responsibilities.
The Priorities
- Establish and communicate a clear vision and strategic direction that aligns mission, programs, funding, partnerships, and internal capacity. Translate strategy into actionable, prioritized work that guides day-to-day decision-making.
- Strengthen the organization’s financial position by improving transparency, broadening the scope of financial reporting, navigating a rapidly changing funding landscape, diversifying revenue, leveraging existing dollars, and aggressively advocating for funding at the local, state, and federal levels.
- Continue to position Worksystems as the convener for the regional workforce system, synthesizing labor market information, interpreting the regional economic context, and partnering resources to achieve regulatory and system obligations.
- Mobilize stakeholders through strategic influence to drive system cohesion and community impact with a dedicated focus on advancing economic mobility and equitable access for our marginalized populations.
- Further align programs and services to ensure mission alignment, financial sustainability, and responsiveness to community and industry needs, while implementing clear KPIs and performance measures to demonstrate impact and guide investment decisions.
- Improve organizational effectiveness by streamlining internal processes, strengthening prioritization and project management, clarifying roles and responsibilities, and building a more integrated, efficient organization that balances strategic work with daily operations.
- Strengthen governance and leadership effectiveness by clarifying roles and decision-making authority, enhancing board engagement and representation, optimizing leadership team performance, and fostering accountability and follow-through across the organization.
- Elevate the organization’s visibility, influence, and credibility by strengthening strategic communications, clearly articulating impact and value, aligning messaging, and ensuring partners and stakeholders understand and support the organization’s role and results.
- Foster a high-performing, resilient organization by strengthening internal communication, addressing personnel and workload challenges, clarifying priorities, investing in staff development, and fostering a culture of accountability, learning, and collaboration.
- Provide strategic oversight of technology and data systems by modernizing infrastructure, improving data management and automation, guiding AI and technology adoption, and determining the future direction of proprietary systems to support sustainability and impact.
The Successful Candidate
The Executive Director is energized by the opportunity to lead Worksystems, serving as a strategic convenor to maximize regional resources and promote the most efficient, accessible, and effective public workforce system. The successful candidate is an exceptional communicator and storyteller, capable of clearly articulating the organization’s mission, vision, strategy, and values internally and externally. They communicate transparently, proactively share information, and deliver consistent, purposeful messaging to multiple audiences, including staff, board members, elected officials, funders, and partners. Importantly, the Executive Director ensures stakeholders understand not only what the organization does, but also why it matters.
The Executive Director demonstrates strong strategic leadership and sound judgment, grounded in big-picture thinking and disciplined prioritization. They establish a clear vision and “north star,” translating strategy into action to guide the organization toward its goals. A thoughtful, measured leader, the Executive Director balances innovation with a deep commitment to strengthening core programs and focuses limited time and resources where they matter most. They also know when to build consensus and when decisive action is required, shifting seamlessly between strategic and operational leadership.
Effective leadership in this role also requires political acumen and external credibility. The Executive Director understands the political, funding, and cultural landscape. They are comfortable engaging with elected officials and advocating persuasively for resources while adhering to compliance and regulatory requirements. A natural convenor and collaborator, the successful candidate forms strong partnerships and builds trust across multiple networks, recognizing that success is rooted in relationships and interdependence. Strong listening skills are equally critical, actively incorporating what they hear into strategy and decision-making. Politically astute yet non-territorial, the Executive Director understands the organization’s role and builds allies to advance shared goals.
Internally, the Executive Director is a people-centered, emotionally intelligent leader who builds trust, empowers staff, and fosters a culture of accountability, learning, and inclusion. They trust and value staff expertise, set clear expectations, and provide teams with the autonomy, feedback, and support needed to deliver results. The successful candidate addresses personnel issues and conflict directly and empathetically, making difficult decisions while sustaining respect and morale. The Executive Director creates clear priorities, develops talent, and ensures staff at all levels understand how their work connects to the broader mission.
Finally, the ideal Executive Director is a resilient, adaptable change leader who thrives in ambiguity and guides the organization through uncertainty with purpose and confidence. They are flexible, nimble, and quick to learn, able to pivot as conditions change while maintaining momentum. An ethical, mission-driven, and values-based leader, the Executive Director brings a fresh perspective and energy without losing sight of history or context. With courage, humility, and follow-through, they inspire others, remove barriers to success, and lead the organization forward, balancing realism with optimism and stability with transformation.
Qualifications
At least ten years of executive leadership experience is required, including experience leading in a complex, multi-stakeholder organization and managing professional, senior-level staff. A diverse background with direct knowledge of the Federal Workforce Innovation and Opportunity Act (WOIA) is essential, as is strong workforce development experience, including public workforce systems. An understanding of how to successfully operate in a highly regulated, compliance-driven environment while supporting forward-thinking innovation is highly desired. Strong financial acumen, with experience managing public funding, along with the ability to navigate multiple funding streams. Prior experience working with a board of directors and with elected officials, policymakers, and government agencies is required. The ability to travel locally, regionally, and nationally as needed is required. The Executive Director is required to live in either Oregon or Washington.
Studies have shown that women and people of color are less likely to apply for jobs unless they believe they can perform every job description task. We are most interested in finding the best candidate for the job, and that candidate may come from a less traditional background. We encourage persons with non-traditional skill sets and experiences to apply, even if you believe you do not meet 100% of the qualifications and hiring criteria described.
Inside Worksystems
Worksystems is a 501(c)(3) non-profit organization that improves the quality of the workforce in the City of Portland and Multnomah and Washington counties. We bring together local elected officials, private sector leaders, public agencies, education, labor, and community-based organizations to understand and address regional workforce challenges and related community issues. By working together, our local economy grows, our pool of homegrown talent grows, and our competitive edge grows.
By design, Worksystems does not deliver direct services to job seekers or workers. Rather, we serve as a strategic convener, coordinator, investor, and broker to maximize regional resources and promote the most efficient, effective public workforce development system. We bridge public and private workforce investments by developing tailored training and education programs designed to meet individuals at their point of need, making a tangible difference in their lives. We ensure the support provided is both meaningful and impactful, delivered by those who truly understand and care for their communities.
Our Mission
Coordinate a regional workforce system that supports individual prosperity and business competitiveness.
Our Goals
- Building a Better System: Ensure the public workforce system in the Portland Metro region is coordinated, equitable, and delivers real results for job seekers, businesses, and community partners.
- Creating Opportunity: Ensure that all job seekers, especially those historically excluded from economic opportunity, have access to the training and support they need to secure quality, family-sustaining jobs.
- Supporting Youth: Ensure that all youth, especially those historically excluded from economic opportunity, gain the skills, experience, and support they need to succeed in the workforce.
- Strengthening Regional Industry: Ensure employers can recruit and retain the talent they need to fill quality jobs through the public workforce system.
Worksystems is authorized under the Federal Workforce Innovation and Opportunity Act of 2014 (WIOA) and is certified by the Governor to represent the region. Worksystems serves as staff to the region’s Workforce Development Board and brings together local elected officials, private-sector leaders, public agencies, education, labor, and community-based organizations to address regional workforce issues and opportunities. Board members are appointed by local elected officials, with a majority representation coming from the private sector. It is the intent of the appointing jurisdictions to ensure the membership of the Workforce Development Board reflects the diversity of the region, the communities we serve, and the justice, equity, diversity, and inclusivity values we support. With a Program Year 2025 Budget of $33.2 million, Worksystems is funded through multiple federal departments, state and regional agencies, counties, cities, and public-private workforce and community funding partners.
For more information, please visit worksystems.org.
Greater Portland
Greater Portland’s livability and wide range of diverse communities make the region especially attractive. People in greater Portland enjoy active, unique, and fulfilling lifestyles enhanced by access to incredible outdoor recreation options and a renowned food and arts scene. Greater Portland is not only the region’s cultural hub, but it also occupies center stage in the state’s positive economic health as a hotbed for a number of industries, including technology, athletic and outdoor apparel, healthcare, and manufacturing.
The Portland metropolitan area is ideally located for quick access to both the ocean and mountains. This location makes it easy for people to enjoy everything the region has to offer, including biking, hiking, trail running, fishing, hunting, boating, golfing, snowboarding, skiing, snowshoeing, surfing, and more. Both the immaculate environment of rugged natural spaces and the culture of outdoor enthusiasts makes greater Portland a nature-lover’s paradise.
Greater Portland is home to trend-setting restaurants, prolific produce, artisan food producers, and a boundary-breaking beverage industry filled with world-class wineries, breweries, and distilleries. The region is also known for food carts dotting the urban landscape, bringing an eclectic mix of flavors and cuisines from around the world.
A hub for art, music, and sports, the area is home to several big-league sports teams. Live theater, museums, galleries, music venues, and magnificent gardens can be found throughout the region. From Portland’s urban core to its rural outskirts, the region hosts all kinds of film, food, beer, wine, and cultural festivals.
Well-being, work-life balance, and health are priorities. Greater Portland is known for making strategic investments in the health of our people, often through collaborative investment projects. With some of the best bicycle infrastructure in the country, the region has invested in greenways, special turn lanes, and bicycle parking to make it easier for people to bike to work, exercise, and make environmentally friendly choices.
Compensation and Benefits
The Executive Director contract is at the discretion of the Board, with an expected salary range of $225,000 - $245,000 annually, and will depend on the qualifications of the successful candidate. Worksystems offers a comprehensive array of valuable benefits to protect employees’ health, family, and way of life. We believe in supporting the whole person, and our benefits reflect taking care of your well-being and that of your loved ones, achieving balance in outside-of-work pursuits, and giving back to the community. Employees also enjoy the day-to-day flexibility of working from home or from our office in downtown Portland. More details can be found here.
How to Apply
Apply electronically through Raftelis. Applicants complete a brief online form and are prompted to provide a cover letter and resume. For full consideration, please apply by Tuesday, February 17, 2026.
Questions
For more information or questions regarding Worksystems or the Executive Director position, please contact Heather Gantz at hgantz@raftelis.com or Robert Colichio at rcolichio@raftelis.com.