Sentry Executive and Leadership Team

September, 2026

Leadership Overview

Sentry has 10 executives leading key functions including corporate strategy, mutual holding oversight, information technology, and regional operations.

Focused on long-term financial stability, Sentry delivers comprehensive property, casualty, and life insurance solutions while maintaining a commitment to policyholder protection and market excellence across the United States.

Leadership Roles at Sentry

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

    Dale Schuh, the Chair and Chief Executive Officer at Sentry, directs the overarching corporate strategy and long-term vision for the organization. Overseeing the board of directors, the Chair and Chief Executive Officer ensures alignment between governance standards and the core mission of providing robust property and casualty insurance products. This leadership role involves managing complex risk portfolios and maintaining the financial health of the enterprise. By prioritizing sustainable growth, Dale Schuh directly impacts the competitive positioning of the firm within the national insurance market. The Chair and Chief Executive Officer maintains rigorous oversight of capital allocation, ensuring that the company remains resilient against market volatility. Through consistent focus on operational excellence, the executive drives the organization toward achieving its primary objectives of policyholder security and fiscal strength, ultimately securing the future of the institution.

    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, manages the structural integrity and strategic direction of the mutual holding entity. Overseeing the broader organizational framework, the Chairman and Chief Executive Officer, Sentry Mutual Holding Company ensures that all subsidiary operations adhere to the foundational principles of mutual ownership and policyholder value. This leadership role involves navigating complex regulatory environments and driving expansion across diverse insurance lines, including life and annuities. By fostering a culture of accountability, Pete McPartland directly influences the long-term viability of the holding company. The Chairman and Chief Executive Officer, Sentry Mutual Holding Company coordinates with executive leadership to optimize asset management and risk mitigation strategies. Through this dedicated focus on institutional stability, the executive secures the company's reputation as a reliable provider of property and casualty insurance solutions.
    Pete McPartland

    Kirk Fritz - Mm and Chief Executive Officer

    Kirk Fritz, the Mm and Chief Executive Officer at Sentry, directs specialized initiatives focused on operational efficiency and market penetration. Overseeing the execution of core business mandates, the Mm and Chief Executive Officer ensures that internal processes support the delivery of high-quality auto and homeowners insurance products. This leadership role involves streamlining cross-departmental workflows to enhance service delivery and customer satisfaction. By implementing data-driven decision-making frameworks, Kirk Fritz directly impacts the operational agility of the firm. The Mm and Chief Executive Officer maintains a sharp focus on identifying emerging market opportunities that align with the company's historical commitment to excellence. Through rigorous management of resources and talent, the executive drives the organization toward achieving superior performance metrics, ensuring that the company remains a leader in the property and casualty sector while maintaining a strong, stable presence in the national insurance landscape.

    Kenneth Krieg - Chief Operating Officer

    Kenneth Krieg, the Chief Operating Officer at Sentry, directs the day-to-day business activities and internal processes that sustain the company's insurance product delivery. Overseeing the coordination between underwriting, claims, and customer service departments, the Chief Operating Officer ensures that operational workflows remain efficient and compliant with industry standards. This leadership role involves optimizing resource allocation to support the company's property and casualty lines. By refining internal procedures, Kenneth Krieg directly impacts the profitability and service quality of the organization. The Chief Operating Officer works closely with regional leadership to ensure that operational strategies are executed consistently across all markets. Through a focus on continuous improvement and process automation, the executive drives the company toward higher levels of productivity, ensuring that the firm remains a reliable partner for homeowners and auto insurance policyholders throughout the United States.

    Jim Frank - Chief Information Officer

    Jim Frank, the Chief Information Officer at Sentry, architects the digital infrastructure and technological roadmap necessary to support modern insurance operations. Overseeing the cybersecurity framework and data analytics platforms, the Chief Information Officer ensures that all digital assets remain secure and accessible for policyholders. This leadership role involves integrating advanced software solutions to automate underwriting processes and improve claims processing speed. By modernizing the technological stack, Jim Frank directly impacts the efficiency of the entire organization. The Chief Information Officer collaborates with other C-suite leaders to align digital transformation efforts with the broader business goals of the company. Through the implementation of scalable cloud solutions, the executive drives innovation across the enterprise, ensuring that the firm maintains a competitive edge in the digital insurance market while providing seamless service experiences to clients across the country.
    Jim Frank

    Paul Boehm - Regional Executive

    Paul Boehm, the Regional Executive at Sentry, directs business development and market growth initiatives within the assigned territory. Overseeing the implementation of regional sales strategies, the Regional Executive ensures that the company's property and casualty insurance products reach target demographics effectively. This leadership role involves building strong relationships with local agents and brokers to expand the market footprint. By analyzing regional market trends, Paul Boehm directly impacts the revenue growth and competitive standing of the firm in the area. The Regional Executive coordinates with corporate headquarters to ensure that national policies are adapted to meet the specific needs of the regional customer base. Through a focus on localized service and strategic outreach, the executive drives the company's expansion efforts, ensuring that the brand remains a trusted name in the insurance industry across the designated geographic region.

    Craig Simonson - Regional Executive

    Craig Simonson, the Regional Executive at Sentry, directs the operational management and client retention efforts within the assigned territory. Overseeing the performance of local insurance portfolios, the Regional Executive ensures that service delivery meets the high standards expected by homeowners and auto insurance clients. This leadership role involves managing regional risk assessments and ensuring that underwriting practices align with corporate guidelines. By fostering strong community connections, Craig Simonson directly impacts the brand loyalty and market share of the firm. The Regional Executive collaborates with regional teams to identify opportunities for product diversification and service enhancement. Through a focus on operational excellence and customer-centric strategies, the executive drives the company's success in the region, ensuring that the firm maintains a robust and profitable presence while delivering consistent value to policyholders across the territory.

    Gerald Heare - Regional Executive

    Gerald Heare, the Regional Executive at Sentry, directs the strategic expansion and operational oversight of insurance services within the assigned territory. Overseeing the development of regional distribution channels, the Regional Executive ensures that the company's life and annuity products are effectively marketed to the target audience. This leadership role involves managing regional sales teams and ensuring that all activities comply with state-level regulations. By optimizing the regional sales funnel, Gerald Heare directly impacts the growth trajectory of the firm. The Regional Executive works to align regional objectives with the broader corporate mission of providing reliable insurance solutions. Through a focus on market analysis and strategic planning, the executive drives the company's competitive performance, ensuring that the firm remains a preferred choice for insurance coverage within the region while maintaining high standards of operational integrity.

    Bob Bordeaux - Regional Executive

    Bob Bordeaux, the Regional Executive at Sentry, directs the execution of regional business plans and the management of local insurance operations. Overseeing the coordination of regional marketing and sales efforts, the Regional Executive ensures that the company's property and casualty lines are positioned for maximum impact. This leadership role involves monitoring regional performance metrics and implementing corrective actions to maintain profitability. By driving engagement with local stakeholders, Bob Bordeaux directly impacts the market presence of the firm. The Regional Executive collaborates with corporate leadership to ensure that regional initiatives support the overall strategic goals of the organization. Through a focus on disciplined execution and market responsiveness, the executive drives the company's growth in the region, ensuring that the firm continues to provide high-quality insurance products and services to a diverse client base.

    Timothy Zepnick - Regional Executive

    Timothy Zepnick, the Regional Executive at Sentry, directs the operational strategy and business development activities within the assigned territory. Overseeing the management of regional insurance portfolios, the Regional Executive ensures that all underwriting and claims processes are handled with precision and efficiency. This leadership role involves identifying regional market opportunities and tailoring product offerings to meet the specific needs of the local population. By optimizing regional operations, Timothy Zepnick directly impacts the financial performance and customer satisfaction levels of the firm. The Regional Executive works to maintain strong relationships with regional partners and clients, ensuring that the company's reputation for reliability remains intact. Through a focus on strategic growth and operational excellence, the executive drives the company's success in the region, ensuring that the firm remains a dominant force in the insurance market.

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    Frequently Asked Questions Regarding Sentry Top Executives and Leadership Team

    Who leads Sentry?
    Sentry is led by Dale Schuh (Chair and Chief Executive Officer), along with executives such as Pete McPartland (Chairman and Chief Executive Officer, Sentry Mutual Holding Company) and Kirk Fritz (Mm and Chief Executive Officer).
    Who is part of Sentry’s executive team?
    The executive team of Sentry includes leaders such as Dale Schuh (Chair and Chief Executive Officer), Pete McPartland (Chairman and Chief Executive Officer, Sentry Mutual Holding Company), Kirk Fritz (Mm and Chief Executive Officer) 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 Chair and Chief Executive Officer, Chairman and Chief Executive Officer, Sentry Mutual Holding Company, Mm and Chief Executive Officer, Chief Operating Officer, Chief Information Officer.