Sentry Executive and Leadership Team

November, 2026

Leadership Overview

Sentry has 10 executives leading key functions including strategy, information technology, operations, and regional market management.

Focused on delivering comprehensive property and casualty coverage, Sentry maintains a commitment to financial stability and policyholder protection through rigorous risk assessment and long-term asset management strategies.

Leadership Roles at Sentry

  • Mm and Chief Executive Officer - Kirk Fritz
  • Chair and Chief Executive Officer - Dale Schuh
  • Chairman and Chief Executive Officer, Sentry Mutual Holding Company - Pete McPartland
  • Chief Operating Officer - Kenneth Krieg
  • Chief Information Officer - Jim Frank
  • Regional Executive - Gerald Heare
  • Regional Executive - Craig Simonson
  • Regional Executive - Timothy Zepnick
  • Regional Executive - Paul Boehm
  • Regional Executive - Bob Bordeaux
  • Kirk Fritz - Mm and Chief Executive Officer

    Kirk Fritz, the Mm and Chief Executive Officer at Sentry, directs the overarching corporate strategy and long-term vision for the organization. Fritz manages the alignment of insurance product development with evolving market demands in the property and casualty sector. By overseeing the integration of life and annuity offerings, the Mm and Chief Executive Officer ensures a diversified portfolio that mitigates risk across various economic cycles. This leadership role involves constant collaboration with the board to maintain fiscal health and operational excellence. Kirk Fritz drives the expansion of service capabilities, ensuring that policyholders receive consistent value. Through the implementation of robust underwriting standards, the Mm and Chief Executive Officer secures the company's position as a reliable provider in the competitive insurance landscape, ultimately fostering sustainable growth and protecting the interests of all stakeholders involved in the enterprise.

    Dale Schuh - Chair and Chief Executive Officer

    Dale Schuh, the Chair and Chief Executive Officer at Sentry, governs the board and provides high-level strategic direction for the entire insurance group. Schuh oversees the governance framework that supports the company's mission of providing reliable property and casualty insurance solutions. The Chair and Chief Executive Officer monitors the performance of core business lines, including homeowners and auto insurance, to ensure alignment with corporate objectives. By facilitating communication between executive leadership and the board, Schuh maintains a focus on long-term stability and capital efficiency. Dale Schuh drives initiatives that enhance the company's market presence while upholding the rigorous standards expected of a major insurance provider. Through the oversight of complex financial structures, the Chair and Chief Executive Officer ensures that the organization remains resilient against market volatility, consistently delivering on promises made to policyholders across the United States.

    Pete McPartland - Chairman and Chief Executive Officer, Sentry Mutual Holding Company

    Pete McPartland, the Chairman and Chief Executive Officer, Sentry Mutual Holding Company at Sentry, leads the holding company structure to ensure the financial integrity of the entire insurance group. McPartland oversees the strategic allocation of capital across various subsidiaries, focusing on the long-term sustainability of property, casualty, and life insurance products. The Chairman and Chief Executive Officer, Sentry Mutual Holding Company manages the relationship with regulatory bodies and stakeholders to maintain the company's reputation for reliability. By driving operational efficiency at the holding level, Pete McPartland ensures that resources are effectively deployed to support regional market growth. This leadership role involves balancing risk management with the pursuit of new business opportunities. Through the guidance of the Chairman and Chief Executive Officer, Sentry Mutual Holding Company, the organization maintains a strong balance sheet, providing the necessary foundation for delivering consistent insurance services to homeowners and businesses nationwide.
    Pete McPartland

    Kenneth Krieg - Chief Operating Officer

    Kenneth Krieg, the Chief Operating Officer at Sentry, manages the day-to-day execution of insurance services and internal business processes. Krieg oversees the operational departments responsible for policy administration, claims management, and customer support across all property and casualty lines. The Chief Operating Officer drives efficiency by streamlining workflows and implementing best practices that enhance service delivery speed. By coordinating with regional teams, Kenneth Krieg ensures that operational standards remain consistent across the entire organization. This leadership role involves monitoring performance metrics to identify areas for improvement and resource optimization. Through the oversight of daily operations, the Chief Operating Officer supports the company's commitment to providing reliable protection for homeowners and businesses. Krieg maintains a focus on operational excellence, ensuring that the infrastructure remains capable of handling high volumes of transactions while maintaining the high quality of service expected from the insurance group.

    Jim Frank - Chief Information Officer

    Jim Frank, the Chief Information Officer at Sentry, architects the digital infrastructure required to support modern insurance operations. Frank oversees the development of secure data systems that facilitate accurate risk assessment and efficient claims processing for property and casualty lines. The Chief Information Officer drives the integration of advanced analytics to improve underwriting precision and customer service delivery. By managing the company's technological roadmap, Frank ensures that digital tools remain scalable and resilient against cyber threats. Jim Frank coordinates with other C-suite leaders to align IT investments with the broader business strategy of the organization. This leadership role involves optimizing internal workflows to reduce administrative overhead and enhance the speed of service. Through the implementation of innovative software solutions, the Chief Information Officer supports the company's mission to provide seamless insurance experiences, ensuring that data-driven insights remain at the core of every business decision.
    Jim Frank

    Gerald Heare - Regional Executive

    Gerald Heare, the Regional Executive at Sentry, directs market-specific operations within the assigned territory to drive growth in property and casualty insurance. Heare oversees the implementation of corporate strategies at the local level, ensuring that product offerings meet the unique needs of the regional customer base. The Regional Executive manages relationships with local agents and brokers to expand the company's footprint in the area. By analyzing regional market trends, Gerald Heare identifies opportunities for increasing market share and improving policyholder retention. This leadership role involves coordinating with the home office to ensure that regional activities align with the broader organizational mission. Through the management of local operations, the Regional Executive supports the company's goal of providing accessible insurance solutions. Heare focuses on building strong community connections, ensuring that the brand remains a trusted partner for homeowners and businesses throughout the designated region.

    Craig Simonson - Regional Executive

    Craig Simonson, the Regional Executive at Sentry, manages the operational performance and business development initiatives within the assigned geographic territory. Simonson oversees the distribution of insurance products, focusing on property and casualty lines that cater to the specific risk profiles of the region. The Regional Executive drives sales growth by fostering partnerships with local distribution channels and enhancing the visibility of the company's offerings. By monitoring regional economic conditions, Craig Simonson adjusts tactical approaches to maintain competitive positioning. This leadership role involves ensuring that service delivery meets the high standards set by the corporate office. Through the oversight of regional activities, the Regional Executive supports the company's mission to provide comprehensive coverage to a diverse client base. Simonson focuses on operational agility, ensuring that the organization can respond effectively to local market shifts while maintaining the financial stability of the insurance group.

    Timothy Zepnick - Regional Executive

    Timothy Zepnick, the Regional Executive at Sentry, leads the strategic execution of insurance services within the assigned market area. Zepnick oversees the management of regional portfolios, ensuring that underwriting practices remain consistent with corporate risk appetite. The Regional Executive drives the expansion of the customer base by identifying underserved segments and tailoring outreach efforts accordingly. By collaborating with local teams, Timothy Zepnick ensures that the company's property and casualty products are effectively marketed and serviced. This leadership role involves managing regional budgets and performance targets to support the overall financial health of the organization. Through the oversight of local operations, the Regional Executive contributes to the company's reputation for reliability and customer-centric service. Zepnick focuses on building long-term relationships with policyholders, ensuring that the insurance group remains a preferred choice for homeowners and businesses in the region.

    Paul Boehm - Regional Executive

    Paul Boehm, the Regional Executive at Sentry, directs the operational and sales activities within the assigned territory to enhance market penetration. Boehm oversees the coordination of regional resources to support the delivery of property and casualty insurance products. The Regional Executive drives the development of local business strategies that align with the company's overarching goals of growth and stability. By engaging with regional stakeholders, Paul Boehm ensures that the company's value proposition is clearly communicated to potential policyholders. This leadership role involves monitoring regional performance metrics and implementing corrective actions to maintain service quality. Through the oversight of regional operations, the Regional Executive supports the company's mission to provide robust insurance protection. Boehm focuses on operational efficiency and market responsiveness, ensuring that the organization remains competitive and capable of meeting the evolving needs of homeowners and businesses across the assigned territory.

    Bob Bordeaux - Regional Executive

    Bob Bordeaux, the Regional Executive at Sentry, manages the regional business operations and strategic initiatives to support the company's presence in the assigned market. Bordeaux oversees the execution of sales and service programs, ensuring that property and casualty insurance products are accessible to the target demographic. The Regional Executive drives the optimization of regional workflows to improve customer satisfaction and operational efficiency. By analyzing local market data, Bob Bordeaux identifies trends that inform the development of effective regional strategies. This leadership role involves collaborating with corporate leadership to ensure that regional activities contribute to the overall success of the insurance group. Through the oversight of local operations, the Regional Executive supports the company's commitment to providing reliable and comprehensive coverage. Bordeaux focuses on building a strong regional presence, ensuring that the organization remains a trusted partner for homeowners and businesses in the area.

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    Frequently Asked Questions Regarding Sentry Top Executives and Leadership Team

    Who leads Sentry?
    Sentry is led by Kirk Fritz (Mm and Chief Executive Officer), along with executives such as Dale Schuh (Chair and Chief Executive Officer) and Pete McPartland (Chairman and Chief Executive Officer, Sentry Mutual Holding Company).
    Who is part of Sentry’s executive team?
    The executive team of Sentry includes leaders such as Kirk Fritz (Mm and Chief Executive Officer), Dale Schuh (Chair and Chief Executive Officer), Pete McPartland (Chairman and Chief Executive Officer, Sentry Mutual Holding Company) and other senior executives.
    How many executives does Sentry have?
    Sentry has 10 executives leading key business areas.
    What roles are included in Sentry’s leadership team?
    The leadership team of Sentry includes roles such as Mm and Chief Executive Officer, Chair and Chief Executive Officer, Chairman and Chief Executive Officer, Sentry Mutual Holding Company, Chief Operating Officer, Chief Information Officer.