Description

Are you a strategic, mission-driven leader ready to make a lasting impact on Washington’s public education system? We are seeking an Executive Director for the Workers’ Compensation Trust and Unemployment Pool—an influential role that supports and strengthens the well-being of school district employees across the region. This is your opportunity to guide a trusted program that safeguards financial integrity, advances innovative claims management, and champions safe, supportive workplaces where staff can thrive. If you excel at building partnerships, driving operational excellence, and delivering meaningful results for the communities we serve, we invite you to join us in shaping a stronger future for our member districts.

The Puget Sound Workers’ Compensation Trust is a self-insured pool for workers’ compensation coverage. The Trust provides insurance for on-the-job injuries for 34 school districts and PSESD and their 45,000 employees in King, Pierce, Skagit, Snohomish and Whatcom counties. Services Districts receive professional claims management services to help injured workers return to the workplace. At the same time, Trust staff work with the employer to assess workplace safety and implement effective loss control programs. Participating school districts own the Trust, with all premiums building equity to help offset costs.  To learn more about PSWCTUP visit https://pswctup.org/. 

PSESD is one of nine regional educational agencies serving school districts and state approved charter and private schools in Washington. Serving over 39% of Washington’s K-12 public school students, our agency provides critical services designed to ensure that our students are ready to enter school, achieve at high levels in the K-12 system, and succeed in postsecondary endeavors. We are committed to becoming an Antiracist Multicultural Organization driven by equity in education. To learn more about PSESD, visit www.psesd.org/about-psesd.

This executive position reports to the Superintendent 

Open until filled, for best consideration submit complete application by date of Sunday, November 23, 2025. Interviews are tentatively scheduled for Tuesday, December 2, 2025. 

Essential Functions

• Collaborates with others to develop and sustain equitable partnerships with PSESD staff, school districts, and advisory board for the purpose of designing and implementing high quality services.
• Compiles data from a wide variety of sources for the purpose of analyzing issues, ensuring compliance with various policies and procedures and/or monitoring program components.
• Convenes and/or facilitates meetings on a variety of issues for the purpose of identifying issues, making recommendations, and/or conveying information to stakeholders.
• Cultivates mutually rewarding relationships with executive advisory boards and trustees of group risk management insurance programs for the purpose of communicating program developments and decision-making that support effective program oversight and governance.
• Develops and maintains an account management framework for the purpose of meeting programmatic customer retention and satisfaction goals as well as business development objectives.
• Develops and executes strategic and operational business plans for the purpose of achieving short-term and long-term goals aligned with the programs’ vision and mission.
• Develops and maintains an annual administrative budget encompassing projection of rates and program costs as directed by ESD policies for the purpose of ensuring programs' solvency and complying with associated regulations.
• Embodies the principles and practices that form our culture for the purpose of meeting the Agency’s End: Success for Each Child.
• Models adaptive leadership practices for the purpose of arriving at a shared understanding of stakeholder roles and responsibilities in developed solutions to risk management challenges.
• Oversees a variety of activities for the purpose of ensuring that program objectives are achieved within budget and in compliance with established regulations.
• Performs personnel functions (e.g., interviewing, evaluating, training, supervising, etc.) for the purpose of maintaining adequate staffing, cultivating a culture that fosters staff engagement and encourages best work, enhancing productivity of personnel, and achieving objectives within budget.
• Represents risk management programs before regulatory, adjudicatory, and governing entities for the purpose of providing information that positions the programs favorably, as well as maintaining the security and integrity of assets.
• Responds to issues and inquiries from school district administrators as well as escalated matters from staff for the purpose of identifying the relevant issues and recommending and/or implementing a solution.
• Secures reinsurance and surety bonds in a timely manner for the purpose of ensuring financial integrity of risk management programs.
• Supervises personnel (e.g., provide coaching and consultation on technical issues, adaptive challenges, personnel matters, strategic opportunities, career goals, professional development, job performance, etc.) for the purpose of advancing the development of effective leaders and high performing teams and achieving agency and departmental objectives.
• Supports and is accountable to an advisory board for the purpose of keeping them appraised of the pool and trust's financial status, trends, and emerging concerns.

Other Functions
Assists other personnel as may be required for the purpose of ensuring an efficient and effective work environment.

Skills, Knowledge, and Abilities

SKILLS are required to perform multiple, technical tasks with a need to periodically upgrade skills in order to meet changing job conditions. Specific skill-based competencies required to satisfactorily perform the functions of the job include: See competencies under Abilities below.

KNOWLEDGE is required to perform algebra and/or geometry; read technical information, compose a variety of documents, and/or facilitate group discussions; and analyze situations to define issues and draw conclusions. Specific knowledge-based competencies required to satisfactorily perform the functions of the job include: See competencies under Abilities below.

ABILITY is required to schedule a number of activities, meetings, and/or events; routinely gather, collate, and/or classify data; and use basic, job-related equipment. Flexibility is required to independently work with others in a wide variety of circumstances; analyze data utilizing a variety of complex processes; and operate equipment using standardized methods. Ability is also required to work with a significant diversity of individuals and/or groups; work with data of widely varied types and/or purposes; and utilize job-related equipment. Independent problem solving is required to analyze issues and create action plans. Problem solving with data requires analysis based on organizational objectives; and problem solving with equipment is limited to moderate.

JOB-SPECIFIC COMPETENCIES

• BUILDING EFFECTIVE TEAMS: Builds a diverse and cohesive team who work together toward shared goals.
• INNOVATION AND CREATIVITY: Generates unique methods, ideas, insights, and connections that challenge the status quo to expand possibilities.
• RISK ANALYSIS AND MANAGEMENT: Identifies, defines and analyzes risks to the Agency, represented districts, programs, staff, and students posed by potential adverse actions or events. Plans, communicates, and implements measures that will avoid, reduce, overcome, or compensate for elements of risk.

VISIONARY: Uses creativity and wisdom to anticipate and plan for the future.

Requirements

Minimum Qualifications
 

• Bachelor’s degree in business administration, finance, public administration, risk management, or a related field. Substantial, progressively responsible experience in a directly related area may substitute for a bachelor’s degree.
• Experience as an executive or senior leadership role in risk management, insurance administration, workers’ compensation, unemployment pool operations, or a comparable self-insured program.
• Demonstrated experience leading diverse teams, managing complex budgets, and developing strategic plans that align with organizational mission and fiscal responsibility.
• Proven ability to foster equitable, trusting, and collaborative relationships with internal and external partners, including boards, member districts, and regulatory agencies.
• Strong knowledge of principles, practices, laws, and regulations related to group self-insurance, workers’ compensation, and unemployment compensation programs.
• Demonstrated skill in analyzing complex data and financial reports, identifying trends and risks, and developing actionable strategies to ensure solvency and sustainability.
• Excellent communication, facilitation, and adaptive leadership skills with the ability to engage in crucial conversations and lead through change.
• Models inclusive and human-centered leadership that cultivates trust and shared accountability across the organization.
   

Preferred Qualifications 

• Experience working within or in partnership with educational institutions, public agencies, or member-based organizations.
• In-depth understanding of Washington State laws and regulatory requirements governing self-insured workers’ compensation programs and unemployment insurance pools.
• Experience working with or supporting a governing or advisory board to shape organizational vision and policy.
• Professional certification in risk management, insurance, or a related discipline (e.g., ARM, CPCU, AIC, SPHR, SHRM-SCP).
• Recognized for leading adaptive change that results in sustainable improvements to organizational culture, structure, and effectiveness.
• Proven record of developing and maintaining partnerships that balance fiduciary responsibility with service excellence and care for the workforce.