Worksystems - Executive Director

Raftelis•Portland, OR

20d•$225,000 - $245,000

About The Position

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 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.

Requirements

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.
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.

Nice To Haves

An understanding of how to successfully operate in a highly regulated, compliance-driven environment while supporting forward-thinking innovation is highly desired.

Responsibilities

Leading and implementing a comprehensive strategic vision
Producing a financially sound budget
Developing and maintaining strong relationships and partnerships
Managing staff
Supporting effective collaboration throughout the region and state
Coordinating and aligning workforce partners to support individual prosperity and advance business competitiveness
Integrating resources, systems, and community priorities into a cohesive and responsive workforce system
Building and sustaining high-impact relationships with funders, partners, and community stakeholders, bridging public and private sectors to strengthen collaboration and outcomes
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
Overseeing efficient day-to-day operations, technology, and compliance with all legal and regulatory requirements, while proactively managing risk and maintaining accountability
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