Westchester Executive and Leadership Team

July, 2026

Leadership Overview

Westchester has 4 executives leading key functions including operations, and strategy.

Driven by a commitment to specialized insurance solutions, Westchester focuses on delivering comprehensive excess and surplus products across diverse risk categories, solidifying its market position through expert underwriting and client-centric service.

Leadership Roles at Westchester

  • Senior Vice President, Chief Operating Officer - Brooke Szewczyk
  • Senior Vice President, Chief Operating Officer, Middle Market P and C - Eric Bouskill
  • President - Ginnie Hays
  • President - Allan Sanderson
  • Brooke Szewczyk - Senior Vice President, Chief Operating Officer

    Brooke Szewczyk, the Senior Vice President, Chief Operating Officer at Westchester, directs the operational framework supporting the company's extensive excess and surplus product lines. Overseeing critical functions across property, specialty casualty, environmental, and professional risk, Szewczyk ensures seamless execution of underwriting strategies and claims processing. This leadership role involves optimizing internal workflows and resource allocation to enhance service delivery for brokers and clients nationwide. By driving efficiency improvements, Brooke Szewczyk directly contributes to Westchester's capacity to manage complex risks and maintain its competitive edge in the insurance market. The focus remains on scalable operations that support continued growth and service excellence across all product offerings, including inland marine and product recall.

    Eric Bouskill - Senior Vice President, Chief Operating Officer, Middle Market P and C

    Eric Bouskill, the Senior Vice President, Chief Operating Officer, Middle Market P and C at Westchester, spearheads the operational strategy for the property and casualty lines targeting the middle market segment. Bouskill's purview encompasses refining underwriting processes, enhancing distribution channel effectiveness, and ensuring robust risk management protocols are in place for this crucial market. This executive drives initiatives aimed at improving operational efficiency and profitability within the middle market P&C portfolio. By fostering strong relationships with brokers and agents, Eric Bouskill ensures Westchester's specialized products meet the evolving needs of middle-market businesses. The operational leadership provided by Bouskill is vital for expanding market penetration and solidifying Westchester's reputation for specialized insurance solutions in this segment.
    Eric Bouskill

    Ginnie Hays - President

    Ginnie Hays, the President at Westchester, provides executive leadership and strategic direction across the organization's diverse insurance offerings. Hays guides the company's vision, focusing on expanding market reach and deepening client relationships within the excess and surplus lines sector. This leadership role involves overseeing all major business units, ensuring alignment with the company's mission to deliver specialized risk solutions. By championing innovation and operational excellence, Ginnie Hays drives the strategic growth of Westchester's property, casualty, environmental, and professional risk portfolios. The focus is on maintaining a high-performance culture that supports superior underwriting and claims services, thereby reinforcing Westchester's position as a trusted partner for complex insurance needs.

    Allan Sanderson - President

    Allan Sanderson, the President at Westchester, directs the overarching strategic initiatives and corporate development for the company's comprehensive suite of excess and surplus products. Sanderson's leadership focuses on identifying new market opportunities and strengthening Westchester's competitive position in specialized insurance segments, including product recall and small business offerings. This executive role involves fostering key partnerships and ensuring the company's strategic objectives are met through effective resource deployment and market analysis. By driving forward-thinking strategies, Allan Sanderson ensures Westchester remains at the forefront of providing tailored solutions for property, specialty casualty, and environmental risks. The emphasis is on sustainable growth and enhancing the value proposition for brokers and insureds across all operational areas.

    Explore Leadership Teams in Insurance

    Frequently Asked Questions Regarding Westchester Top Executives and Leadership Team

    Who leads Westchester?
    Westchester is led by Brooke Szewczyk (Senior Vice President, Chief Operating Officer), along with executives such as Eric Bouskill (Senior Vice President, Chief Operating Officer, Middle Market P and C) and Ginnie Hays (President).
    Who is part of Westchester’s executive team?
    The executive team of Westchester includes leaders such as Brooke Szewczyk (Senior Vice President, Chief Operating Officer), Eric Bouskill (Senior Vice President, Chief Operating Officer, Middle Market P and C), Ginnie Hays (President) and other senior executives.
    How many executives does Westchester have?
    Westchester has 4 executives leading key business areas.
    What roles are included in Westchester’s leadership team?
    The leadership team of Westchester includes roles such as Senior Vice President, Chief Operating Officer, Senior Vice President, Chief Operating Officer, Middle Market P and C, President, President.