Westfield Insurance Executive and Leadership Team

September, 2026

Leadership Overview

Westfield Insurance has 4 executives leading key functions including strategy, operations, administration, and legal compliance.

Focused on delivering comprehensive protection, Westfield Insurance maintains a commitment to personal, business, and agribusiness insurance excellence while driving long-term stability across the United States insurance market.

Leadership Roles at Westfield Insurance

  • Chief Executive Officer - Gregory Galeaz
  • Chief Operations Officer - Brad Kass
  • Chief Administrative Officer (CAO) - Anthony Chimera
  • Chief Legal Officer & Secretary - Frank Carrino
  • Gregory Galeaz - Chief Executive Officer

    Gregory Galeaz, the Chief Executive Officer at Westfield Insurance, directs the overarching corporate strategy and long-term vision for the organization. By aligning business objectives with the evolving needs of personal, business, and agribusiness policyholders, the Chief Executive Officer ensures consistent growth and market relevance. This leadership role involves constant collaboration with the Board to refine risk management frameworks and capital allocation. Gregory Galeaz monitors national market trends to maintain a competitive edge in the insurance sector. Through the oversight of high-level performance metrics, the Chief Executive Officer drives operational excellence across all regional divisions. By fostering a culture of innovation and accountability, the Chief Executive Officer secures the financial health of the enterprise. Ultimately, Galeaz positions the company for sustainable success while navigating complex regulatory environments and shifting consumer demands within the broader insurance landscape.

    Brad Kass - Chief Operations Officer

    Brad Kass, the Chief Operations Officer at Westfield Insurance, manages the daily execution of insurance service delivery and internal process optimization. Overseeing the infrastructure supporting personal and business policy administration, the Chief Operations Officer ensures seamless workflows across all departments. This role requires constant coordination with technology teams to modernize digital platforms and improve customer experience. Brad Kass drives efficiency by streamlining claims processing and underwriting procedures to reduce overhead costs. By analyzing operational data, the Chief Operations Officer identifies bottlenecks and implements scalable solutions to support business expansion. The Chief Operations Officer maintains rigorous standards for service quality, ensuring that every policyholder receives timely and accurate support. Through the management of cross-functional teams, Kass optimizes resource allocation to meet aggressive performance targets. Ultimately, Kass strengthens the operational backbone of the organization to support long-term growth objectives.

    Anthony Chimera - Chief Administrative Officer (CAO)

    Anthony Chimera, the Chief Administrative Officer (CAO) at Westfield Insurance, directs the internal support functions and organizational development initiatives. Overseeing human resources, facilities management, and corporate communications, the Chief Administrative Officer (CAO) ensures that the internal environment aligns with the broader mission of the company. This leadership role involves architecting talent acquisition strategies to attract top-tier professionals in the insurance industry. Anthony Chimera manages the integration of corporate culture across all regional offices to maintain high employee engagement and productivity. By optimizing administrative workflows, the Chief Administrative Officer (CAO) reduces operational friction and enhances organizational agility. The Chief Administrative Officer (CAO) collaborates with other C-suite leaders to implement enterprise-wide policies that support sustainable growth. Through the oversight of internal infrastructure, Chimera ensures that the company remains well-positioned to handle the complexities of the modern insurance market while maintaining a focus on long-term stability.
    Frank Carrino, the Chief Legal Officer & Secretary at Westfield Insurance, directs all legal affairs, corporate governance, and regulatory compliance initiatives. Overseeing the legal department, the Chief Legal Officer & Secretary ensures that all insurance products and business practices adhere to state and federal mandates. This role involves managing complex litigation, contract negotiations, and risk mitigation strategies to protect the assets of the organization. Frank Carrino provides critical counsel to the Board regarding corporate governance and fiduciary responsibilities. By monitoring legislative changes, the Chief Legal Officer & Secretary proactively adjusts internal policies to maintain full compliance across all jurisdictions. The Chief Legal Officer & Secretary works closely with executive leadership to navigate legal challenges associated with agribusiness and personal insurance offerings. Through the management of external counsel and internal legal teams, Carrino safeguards the reputation and legal standing of the company in a highly regulated industry.
    Frank Carrino

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    Frequently Asked Questions Regarding Westfield Insurance Top Executives and Leadership Team

    Who leads Westfield Insurance?
    Westfield Insurance is led by Gregory Galeaz (Chief Executive Officer), along with executives such as Brad Kass (Chief Operations Officer) and Anthony Chimera (Chief Administrative Officer (CAO)).
    Who is part of Westfield Insurance’s executive team?
    The executive team of Westfield Insurance includes leaders such as Gregory Galeaz (Chief Executive Officer), Brad Kass (Chief Operations Officer), Anthony Chimera (Chief Administrative Officer (CAO)) and other senior executives.
    How many executives does Westfield Insurance have?
    Westfield Insurance has 4 executives leading key business areas.
    What roles are included in Westfield Insurance’s leadership team?
    The leadership team of Westfield Insurance includes roles such as Chief Executive Officer, Chief Operations Officer, Chief Administrative Officer (CAO), Chief Legal Officer & Secretary.