Executive Director

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.

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. 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.

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. 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.

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. 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.

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…