Job Details

Chief Executive Officer (CEO)

About the Opportunity

The PLF is seeking a Chief Executive Officer to serve as both steward and leader of this unique institution. The CEO role is central to maintaining the PLF’s credibility—with its covered legal practitioners, the courts, the Oregon State Bar, and the public—while ensuring the organization remains operationally sound, financially sustainable, and culturally strong.

This is a role for a senior executive who is comfortable operating in governance-intensive legal and quasi-public environments, who understands the importance of expert judgment, and who can lead through complexity without unnecessary centralization or disruption. The CEO is expected to provide calm, consistent leadership; clear decision-making; and visible fairness, particularly in moments of stress or external scrutiny.
 

What You Will Do

LEAD A COMPLEX, EXPERT ORGANIZATION

• Serve as a leader of managers, setting clear expectations for performance, conduct, communication, and accountability across the organization.
• Coach and support senior leaders, ensuring they are aligned, effective, and equipped to lead their teams.
• Address any performance, behavior, and organizational issues promptly and fairly, with attention to both legal risk and organizational trust.
• Foster an environment of foundational trust where employees feel able to raise concerns, offer dissenting views, and provide candid feedback.
• Explicitly protect professional and clinical autonomy—particularly in claims judgment and OAAP operations—while reinforcing clear reporting lines and decision rights.

STRENGTHEN OPERATIONAL CLARITY AND EXECUTION

• Provide strong governance of claims handling and litigation/coverage judgment.
• Maintain and refine a clear operating framework that defines decision-making authority, role boundaries, escalation paths, and expectations for collaboration.
• Support meeting discipline, executive communications, and cross-functional project management to increase predictability and follow-through.
• Balance respect for existing, effective processes with targeted improvements where clarity, efficiency, or consistency can be strengthened.
• Sequence any organizational change thoughtfully, ensuring stability first and avoiding unnecessary churn or fatigue.

PROVIDE STRATEGIC LEADERSHIP

• Translate the PLF’s statutory mission and PLF Board priorities into a limited set of clear, measurable organizational outcomes.
• Apply systems thinking to decisions, integrating legal, financial, operational, and human considerations.
• Anticipate downstream effects of decisions on staff, covered practitioners, the OSB, the courts, and external partners.
• Regularly assess organizational capacity and pace, adjusting expectations as needed to maintain quality and morale.

ACT AS STEWARD

• Work closely with the PLF Board and finance leadership to ensure sound budgeting, internal controls, investment oversight, and long-term sustainability.
• Communicate financial information in plain language to ensure shared understanding among PLF Board members and senior leaders.
• Protect the PLF’s funding model and reputation by managing external risks related to regulation, reinsurance, litigation outcomes, and workforce stability.

MANAGE GOVERNANCE AND EXTERNAL RELATIONSHIPS

• Maintain a transparent, constructive relationship with the PLF Board, with clear boundaries between governance and management.
• Engage effectively with reinsurance brokers, auditors, regulators, and external counsel.
• Represent the PLF credibly with the OSB, the judiciary, legislators, and the broader legal community.
• Navigate the PLF–OSB relationship as a collaborative partnership without compromising PLF’s independent judgment or authority.

What We’re Seeking

EXECUTIVE EXPERIENCE AND JUDGMENT

• Significant senior executive experience leading professional or expert-driven organizations, preferably in public or quasi-public environments.
• Demonstrated success operating within governance-intensive environments, including regular interaction with a Board or similar oversight body.
• Experience making high-stakes decisions that balance legal risk, financial exposure, and organizational impact to ensure organizational resilience.

PEOPLE LEADERSHIP AND ORGANIZATIONAL MATURITY

• A clear track record as a leader of managers, including setting standards, coaching leaders, and holding people responsible with consistency and fairness.
• Comfort addressing complex and sensitive personnel issues, with an understanding of sound human resources practices.
• Ability to unify leadership teams with differing perspectives and professional styles.

LEGAL, INSURANCE, AND FINANCIAL ACUMEN

• Credible experience in at least one of the following areas: complex civil litigation, professional liability insurance, or claims or coverage governance.
• Sufficient financial literacy to partner effectively with finance professionals and the PLF Board on budgets, investments, and controls.
• Ability to explain insurance and financial concepts clearly to non-specialist audiences.

COMMUNICATION AND PRESENCE

• Strong written and verbal communication skills, with the ability to convey difficult or technical topics in clear, accessible language.
• Demonstrates an executive presence grounded in calm communication, clear thinking, active listening, and timely, well‑judged decision‑making.
• A reputation for integrity, discretion, and sound judgment.

Advanced degrees (JD, MBA, MPA, or similar) are preferred, but substantial equivalent experience will be given equal consideration.
 

Why This Role Matters

The PLF exists to serve the Oregon legal profession. Leading this organization is not about transformation for its own sake or personal visibility. It is about stewardship—protecting what works, addressing what truly needs attention, and ensuring the PLF continues to meet its mandate with professionalism and credibility.

 

How To Express Interest

If you’re an executive who values thoughtful leadership, public service, and the opportunity to make a durable contribution to the legal system, the PLF CEO role offers a uniquely meaningful and demanding opportunity.

We encourage you to express interest by reaching out to us at Boly:Welch at 503.242.1300 or by reaching out directly to Kelsey or Kristina by May 15, 2026.

KRISTINA KALKMAN                            
Executive Search Consultant                  
[email protected]                         
503.867.6375                                           

KELSEY WILLIAMS, J.D.
Attorney Recruiter
[email protected]
406.552.2411