ProAssurance Executive and Leadership Team

September, 2026

Leadership Overview

ProAssurance has 4 executives leading key functions including marketing strategy, claims management, workers' compensation insurance, and specialized program development.

Focused on delivering robust medical professional liability solutions, ProAssurance maintains a commitment to financial stability and collaborative risk management for healthcare providers across the United States.

Leadership Roles at ProAssurance

  • Chief Claims Officer & Co-President & Group Liability Professional - Darryl Thomas
  • President, Workers' Compensation Insurance - Kevin Shook
  • President, Pica Programs - Margaret Christian
  • Chief Marketing Officer - Jeff Bowlby
  • Darryl Thomas - Chief Claims Officer & Co-President & Group Liability Professional

    Darryl Thomas, the Chief Claims Officer & Co-President & Group Liability Professional at ProAssurance, oversees the entire lifecycle of medical professional liability claims. Managing complex litigation and settlement processes, the Chief Claims Officer & Co-President & Group Liability Professional ensures fair and collaborative outcomes for healthcare providers. This leadership role requires deep technical knowledge of liability frameworks and the ability to mitigate financial exposure for the organization. Darryl Thomas coordinates with legal teams and risk management experts to resolve disputes efficiently. By maintaining rigorous standards in claims handling, the Chief Claims Officer & Co-President & Group Liability Professional protects the financial integrity of the company. The operational scope includes broad oversight of liability portfolios across various healthcare sectors. Through proactive claims management, the Chief Claims Officer & Co-President & Group Liability Professional supports the long-term stability of the insurance group while upholding the reputation of the firm as a reliable partner for medical professionals.
    Darryl Thomas

    Kevin Shook - President, Workers' Compensation Insurance

    Kevin Shook, the President, Workers' Compensation Insurance at ProAssurance, directs the strategic development and underwriting of workers' compensation products. Overseeing regional operations, the President, Workers' Compensation Insurance ensures that coverage solutions meet the specific needs of healthcare organizations and related entities. This leadership role involves managing risk assessment protocols and optimizing the performance of the workers' compensation portfolio. Kevin Shook collaborates with the executive team to align product offerings with the broader mission of providing financial security to policyholders. By monitoring market shifts and regulatory changes, the President, Workers' Compensation Insurance maintains a robust and compliant underwriting framework. The operational focus includes driving efficiency in policy administration and claims processing to enhance service delivery. Through disciplined risk selection and strategic growth initiatives, the President, Workers' Compensation Insurance strengthens the market position of the company within the competitive workers' compensation sector.
    Kevin Shook

    Margaret Christian - President, Pica Programs

    Margaret Christian, the President, Pica Programs at ProAssurance, manages the specialized insurance programs designed for niche healthcare markets. Architecting tailored coverage solutions, the President, Pica Programs ensures that unique risk profiles receive appropriate underwriting attention and support. This leadership role involves overseeing the development of specialized insurance products that complement the core medical professional liability offerings. Margaret Christian drives the expansion of these programs by identifying emerging needs within the healthcare industry. By coordinating with internal teams and external partners, the President, Pica Programs maintains high standards of service and risk management. The operational scale involves managing program performance across diverse geographic regions to ensure consistent profitability and growth. Through strategic oversight of these specialized initiatives, the President, Pica Programs contributes significantly to the overall diversification and resilience of the company. Margaret Christian ensures that every program aligns with the overarching commitment to providing expert insurance solutions to healthcare providers.
    Margaret Christian

    Jeff Bowlby - Chief Marketing Officer

    Jeff Bowlby, the Chief Marketing Officer at ProAssurance, directs all brand positioning and market outreach initiatives for the specialty insurance group. By analyzing healthcare sector trends, the Chief Marketing Officer architects comprehensive communication strategies that highlight the firm's underwriting expertise. This leadership role involves managing the public perception of medical professional liability products while ensuring alignment with corporate growth objectives. Jeff Bowlby drives engagement across diverse healthcare systems, from individual practitioners to large-scale organizations. Through the implementation of data-driven campaigns, the Chief Marketing Officer expands the reach of risk management services. By fostering strong relationships with brokers and policyholders, the marketing department secures a competitive advantage in the insurance marketplace. Ultimately, the Chief Marketing Officer ensures that the value proposition of the company remains clear and compelling to all stakeholders within the complex medical liability landscape.
    Jeff Bowlby

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    Frequently Asked Questions Regarding ProAssurance Top Executives and Leadership Team

    Who leads ProAssurance?
    ProAssurance is led by Darryl Thomas (Chief Claims Officer & Co-President & Group Liability Professional), along with executives such as Kevin Shook (President, Workers' Compensation Insurance) and Margaret Christian (President, Pica Programs).
    Who is part of ProAssurance’s executive team?
    The executive team of ProAssurance includes leaders such as Darryl Thomas (Chief Claims Officer & Co-President & Group Liability Professional), Kevin Shook (President, Workers' Compensation Insurance), Margaret Christian (President, Pica Programs) and other senior executives.
    How many executives does ProAssurance have?
    ProAssurance has 4 executives leading key business areas.
    What roles are included in ProAssurance’s leadership team?
    The leadership team of ProAssurance includes roles such as Chief Claims Officer & Co-President & Group Liability Professional, President, Workers' Compensation Insurance, President, Pica Programs, Chief Marketing Officer.