Westchester Executive and Leadership Team

David Roberts, the Chief Operating Officer at Westchester, directs the internal infrastructure and administrative workflows necessary for high-volume surplus lines insurance. Roberts oversees the integration of technology platforms to streamline underwriting processes for property and specialty casualty products. By optimizing operational efficiency, the Chief Operating Officer ensures that internal resources align with the broader corporate objective of maintaining market agility. This leadership role involves constant collaboration with the underwriting teams to refine service delivery models across North American markets. David Roberts monitors performance metrics to identify bottlenecks in policy issuance and claims processing. Through rigorous oversight of internal systems, the Chief Operating Officer drives sustainable growth and maintains the high standards of service expected by brokers and clients. Roberts secures the operational foundation required for the company to navigate the complexities of the excess and surplus insurance landscape effectively.

Eric Bouskill, the Senior Vice President, Chief Operating Officer, Middle Market P and C at Westchester, manages the strategic execution of middle market property and casualty insurance initiatives. Bouskill architects specialized underwriting frameworks designed to address the unique risk profiles of small business and professional risk clients. By focusing on the middle market segment, the Senior Vice President, Chief Operating Officer, Middle Market P and C ensures that product offerings remain competitive and responsive to evolving industry demands. This role requires close coordination with regional sales teams to expand the footprint of inland marine and environmental insurance solutions. Eric Bouskill analyzes market trends to adjust risk appetite and pricing strategies accordingly. Through the implementation of targeted growth initiatives, the Senior Vice President, Chief Operating Officer, Middle Market P and C strengthens the company's position as a leader in the surplus lines sector while maintaining strict underwriting discipline.

Brooke Szewczyk, the Senior Vice President, Chief Operating Officer at Westchester, leads the strategic development of product recall and specialty casualty insurance programs. Szewczyk oversees the cross-functional teams responsible for product innovation and market expansion, ensuring that the company addresses emerging risks with precision. By refining the operational approach to complex professional risk portfolios, the Senior Vice President, Chief Operating Officer drives significant improvements in underwriting accuracy and client satisfaction. This leadership position involves managing relationships with key stakeholders to ensure that product recall solutions meet the rigorous demands of modern industry. Brooke Szewczyk evaluates operational performance to enhance the speed and reliability of service delivery across all specialty lines. Through the application of data-driven insights, the Senior Vice President, Chief Operating Officer optimizes the allocation of resources to support long-term profitability and market stability within the competitive insurance environment.

Allan Sanderson, the President at Westchester, defines the overarching strategic vision and market positioning for the entire organization. Sanderson directs the executive leadership team to ensure alignment across all product lines, including property, specialty casualty, and environmental insurance. By fostering a culture of underwriting excellence, the President maintains the company's reputation for providing robust excess and surplus solutions. This role involves engaging with the Board to set long-term financial targets and growth objectives that reflect the company's commitment to the insurance industry. Allan Sanderson monitors the competitive landscape to identify opportunities for expansion and diversification of the product portfolio. Through the active management of corporate governance and strategic partnerships, the President ensures that the organization remains resilient in the face of global market fluctuations. Sanderson drives the company toward sustained success by prioritizing innovation and operational integrity in every facet of the business.

Ginnie Hays, the President at Westchester, oversees the execution of high-level business strategies focused on inland marine and professional risk insurance segments. Hays directs the development of specialized underwriting capabilities that allow the company to capture market share in complex risk categories. By coordinating with department heads, the President ensures that operational activities support the broader mission of delivering superior surplus lines products. This leadership role involves analyzing regional market performance to guide the expansion of service offerings across diverse geographic territories. Ginnie Hays champions initiatives that improve the efficiency of the underwriting process, thereby enhancing the value provided to brokers and policyholders. Through the strategic oversight of resource management and talent development, the President strengthens the organizational capacity to handle intricate insurance challenges. Hays secures the company's competitive advantage by maintaining a sharp focus on underwriting quality and client-centric service delivery.