Westchester Executive and Leadership Team

June, 2026

Leadership Overview

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

Driven by a commitment to specialized insurance solutions, Westchester focuses on delivering tailored excess and surplus products across diverse risk categories, solidifying its market position through expert risk management 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 & 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 comprehensive 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 policyholders nationwide. By driving efficiency improvements, Brooke Szewczyk directly contributes to Westchester's capacity to manage complex risks and maintain a competitive edge in the insurance market. The focus remains on scalable operations that support sustained growth and robust financial performance across all product segments.

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

    Eric Bouskill, the Senior Vice President, Chief Operating Officer, Middle Market P & C at Westchester, spearheads the operational execution for the property and casualty lines targeting the middle market segment. Bouskill's purview encompasses refining underwriting processes, claims management, and service delivery specifically for this crucial business sector. This involves close collaboration with underwriting teams to ensure product competitiveness and responsiveness to market demands. By focusing on operational excellence within the middle market P&C division, Eric Bouskill drives the strategic implementation of policies and procedures that enhance profitability and client satisfaction. The objective is to solidify Westchester's presence and expand market share through efficient and effective operational leadership in this key area.
    Eric Bouskill

    Ginnie Hays - President

    Ginnie Hays, the President at Westchester, provides overarching strategic direction and executive leadership for the organization's diverse insurance offerings. Hays's mandate includes shaping the company's vision, fostering a culture of innovation, and ensuring alignment across all business units, from property and specialty casualty to professional risk and product recall. This leadership position involves guiding market expansion initiatives and strengthening broker relationships across North America. By setting the strategic course, Ginnie Hays drives the company's commitment to providing specialized excess and surplus solutions. The focus is on sustainable growth, operational integrity, and maintaining Westchester's reputation as a trusted partner in complex insurance markets.

    Allan Sanderson - President

    Allan Sanderson, the President at Westchester, directs the strategic initiatives and operational performance across the company's extensive portfolio of excess and surplus insurance products. Sanderson's leadership encompasses driving growth in key segments such as environmental, inland marine, and small business insurance, while ensuring robust underwriting practices. This role involves fostering strong relationships with distribution partners and guiding the development of innovative risk management solutions. By championing strategic priorities, Allan Sanderson ensures that Westchester effectively addresses the evolving needs of its clients and maintains its position as a leader in specialized insurance. The emphasis is on long-term value creation and operational excellence throughout the organization.

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    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 & 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 & 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 & C, President, President.