Sentry Executive and Leadership Team

May, 2026

Leadership Overview

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

Driven by a commitment to customer service, Sentry provides a comprehensive suite of insurance products, focusing on property and casualty, auto, and life insurance to meet diverse client needs.

Leadership Roles at Sentry

  • Chairman and Chief Executive Officer, Sentry Mutual Holding Company - Pete McPartland
  • Chief Operating Officer - Kenneth Krieg
  • President - John Hyland
  • Regional President, National Accounts, Transportation & Insurance - Scott Miller
  • Chief Information Officer - Jim Frank
  • Regional Executive - Paul Boehm
  • Regional Executive - Much Heare
  • Regional Executive - Bob Bordeaux
  • Regional Executive - Timothy Zepnick
  • Regional Executive - Roger Kaland
  • 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, directs the overarching corporate strategy and operational execution. This leadership role involves guiding the company's direction in offering a broad spectrum of insurance products, encompassing auto, homeowners, and other property and casualty lines, alongside life and annuities. McPartland's oversight ensures alignment with the company's mission to provide reliable insurance solutions. The Chairman and Chief Executive Officer, Sentry Mutual Holding Company drives the organization's financial performance and market positioning. By fostering a culture of integrity and customer focus, Pete McPartland ensures Sentry maintains its strong reputation and commitment to policyholders. This executive leadership is crucial for navigating the complexities of the insurance industry and achieving sustainable growth across all business segments.
    Pete McPartland

    Kenneth Krieg - Chief Operating Officer

    Kenneth Krieg, the Chief Operating Officer at Sentry, directs the day-to-day operational functions across the organization. This encompasses managing the efficiency and effectiveness of processes related to underwriting, claims, and customer service for property and casualty, auto, and homeowners insurance. The Chief Operating Officer ensures seamless integration of operations supporting life and annuity products. Krieg's focus is on optimizing workflows and resource allocation to enhance service delivery and profitability. By driving operational excellence, Kenneth Krieg supports Sentry's strategic objectives and market competitiveness. This leadership position is vital for maintaining high standards in policy administration and claims handling, ensuring policyholder satisfaction and operational resilience.

    John Hyland - President

    John Hyland, the President at Sentry, leads key strategic initiatives and operational oversight across various business units. This role involves driving growth and innovation in the company's comprehensive insurance portfolio, including auto, homeowners, and property and casualty lines. The President ensures alignment between departmental objectives and the broader corporate vision. Hyland's leadership focuses on enhancing market presence and customer engagement for life and annuity products. By fostering collaboration among executive teams, John Hyland supports the development and execution of strategic plans. This executive position is critical for guiding Sentry's expansion and maintaining its commitment to providing exceptional insurance services and financial security to policyholders.

    Scott Miller - Regional President, National Accounts, Transportation & Insurance

    Scott Miller, the Regional President, National Accounts, Transportation & Insurance at Sentry, leads strategic engagement with key national accounts and specialized sectors. This involves driving the development and delivery of tailored insurance solutions for transportation clients and large enterprises across property and casualty, auto, and homeowners lines. The Regional President, National Accounts, Transportation & Insurance ensures comprehensive coverage and service excellence for these critical segments, including life and annuity considerations. Miller's expertise focuses on cultivating long-term partnerships and expanding Sentry's footprint within these specialized markets. By overseeing these high-value accounts, Scott Miller significantly contributes to Sentry's revenue growth and market leadership in targeted industries.

    Jim Frank - Chief Information Officer

    Jim Frank, the Chief Information Officer at Sentry, architects and executes the company's technology strategy. This involves overseeing all aspects of information systems, digital infrastructure, and cybersecurity to support Sentry's diverse insurance offerings. The Chief Information Officer ensures that technology solutions enhance operational efficiency and customer experience across auto, homeowners, and property and casualty lines. Frank's leadership drives innovation in data management and system integration, critical for the company's continued growth. By managing technological resources effectively, Jim Frank supports the seamless delivery of life and annuity products. This role is pivotal in maintaining the integrity and security of Sentry's digital assets, safeguarding policyholder information and enabling robust business operations.
    Jim Frank

    Paul Boehm - Regional Executive

    Paul Boehm, the Regional Executive at Sentry, spearheads market development and client relations within a designated geographic area. This involves driving the sales and service of Sentry's diverse insurance products, including auto, homeowners, and property and casualty lines, across the region. The Regional Executive ensures localized strategies align with national objectives for life and annuity offerings. Boehm's responsibilities include building strong partnerships with agents and brokers, expanding market share, and ensuring customer satisfaction. By overseeing regional operations, Paul Boehm contributes significantly to Sentry's overall growth and market penetration. This role is essential for adapting Sentry's comprehensive insurance solutions to meet the specific needs of regional policyholders.

    Much Heare - Regional Executive

    Much Heare, the Regional Executive at Sentry, manages and expands the company's presence in a specific geographic territory. This leadership function involves overseeing the delivery of Sentry's extensive insurance products, such as auto, homeowners, and property and casualty lines, to regional clients. The Regional Executive ensures that local market demands are met while upholding Sentry's standards for life and annuity products. Heare's focus is on cultivating strong relationships with policyholders and distribution partners, driving revenue growth and market penetration. By directing regional sales and service efforts, Much Heare plays a vital role in Sentry's national strategy. This position is key to adapting Sentry's insurance solutions effectively within the assigned market.

    Bob Bordeaux - Regional Executive

    Bob Bordeaux, the Regional Executive at Sentry, directs market strategy and operational execution within a defined geographical area. This role involves driving the successful distribution of Sentry's comprehensive insurance offerings, including auto, homeowners, and property and casualty lines, to regional customers. The Regional Executive ensures that local market dynamics are addressed for life and annuity products, fostering client retention and acquisition. Bordeaux's leadership focuses on building robust agent networks and enhancing customer service levels. By managing regional performance, Bob Bordeaux contributes directly to Sentry's expansion and its commitment to providing reliable insurance coverage. This executive function is critical for tailoring Sentry's value proposition to diverse regional needs.

    Timothy Zepnick - Regional Executive

    Timothy Zepnick, the Regional Executive at Sentry, oversees market penetration and client engagement within a specific territory. This leadership position involves driving the sales and service of Sentry's broad insurance portfolio, including auto, homeowners, and property and casualty lines, to meet regional demands. The Regional Executive ensures effective delivery of life and annuity products, adapting strategies to local market conditions. Zepnick's responsibilities include fostering strong relationships with policyholders and distribution partners, thereby enhancing Sentry's regional market share. By managing regional operations, Timothy Zepnick plays a crucial role in Sentry's overall growth strategy and its commitment to providing dependable insurance solutions.

    Roger Kaland - Regional Executive

    Roger Kaland, the Regional Executive at Sentry, directs regional business development and client relationship management. This role involves driving the effective distribution of Sentry's comprehensive insurance products, encompassing auto, homeowners, and property and casualty lines, within the assigned territory. The Regional Executive ensures that Sentry's life and annuity offerings are strategically presented to meet regional client needs. Kaland's focus is on expanding market reach and ensuring high levels of customer satisfaction through localized service initiatives. By leading regional teams, Roger Kaland significantly contributes to Sentry's growth objectives and its reputation for reliable insurance services. This executive function is vital for adapting Sentry's solutions to diverse regional markets.

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    Frequently Asked Questions Regarding Sentry Top Executives and Leadership Team

    Who leads Sentry?
    Sentry is led by Pete McPartland (Chairman and Chief Executive Officer, Sentry Mutual Holding Company), along with executives such as Kenneth Krieg (Chief Operating Officer) and John Hyland (President).
    Who is part of Sentry’s executive team?
    The executive team of Sentry includes leaders such as Pete McPartland (Chairman and Chief Executive Officer, Sentry Mutual Holding Company), Kenneth Krieg (Chief Operating Officer), John Hyland (President) 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 Chairman and Chief Executive Officer, Sentry Mutual Holding Company, Chief Operating Officer, President, Regional President, National Accounts, Transportation & Insurance, Chief Information Officer.