Westchester Executive and Leadership Team

July, 2026

Leadership Overview

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

Driven by a commitment to specialized insurance solutions, Westchester focuses on delivering excess and surplus products across a diverse range of risks, solidifying its market position through expert underwriting and client-focused 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 such as underwriting support, claims processing, and policy administration, Szewczyk ensures operational efficiency across property, specialty casualty, environmental, and professional risk portfolios. This leadership role involves optimizing internal processes to enhance service delivery for brokers and clients navigating complex insurance needs. By driving process improvements and resource allocation, Brooke Szewczyk directly impacts the company's ability to manage risk effectively and maintain a competitive edge in the specialized insurance market. The focus remains on scalable operations that support Westchester's broad product offerings and geographic reach.

    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 includes refining underwriting workflows, managing broker relationships, and ensuring the seamless delivery of specialized insurance solutions for this key demographic. This executive drives initiatives aimed at enhancing the profitability and market penetration of Westchester's middle market P and C offerings. By focusing on operational excellence and market responsiveness, Eric Bouskill ensures that the company effectively addresses the unique risk exposures faced by middle-market businesses. The strategic objective involves expanding market share through efficient operations and tailored product delivery.
    Eric Bouskill

    Ginnie Hays - President

    Ginnie Hays, the President at Westchester, provides executive leadership and strategic direction across the organization's diverse insurance product lines. Hays guides the overarching vision for Westchester's excess and surplus offerings, including property, specialty casualty, environmental, and professional risk. This leadership position involves fostering a culture of innovation and client advocacy, ensuring the company remains at the forefront of specialized insurance solutions. By collaborating with key stakeholders and driving strategic initiatives, Ginnie Hays strengthens Westchester's market presence and commitment to underwriting excellence. The focus is on sustainable growth and expanding the company's capacity to serve complex risk needs across various industries.

    Allan Sanderson - President

    Allan Sanderson, the President at Westchester, directs the strategic growth and market positioning for the company's comprehensive suite of excess and surplus insurance products. Sanderson's leadership encompasses driving innovation in product development and expanding market reach for property, specialty casualty, environmental, and professional risk lines. This executive role involves cultivating strong relationships with brokers and partners, ensuring Westchester consistently delivers expert solutions for challenging insurance needs. By championing strategic partnerships and operational enhancements, Allan Sanderson reinforces the company's reputation for reliability and specialized expertise. The objective is to enhance market share and solidify Westchester's position as a leading provider in the E&S sector.

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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 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.