Sentry Executive and Leadership Team

August, 2026

Leadership Overview

Sentry has 9 executives leading key functions including corporate strategy, mutual holding oversight, information technology, operations, and regional market management.

Committed to protecting policyholders through comprehensive property and casualty coverage, Sentry maintains a century-long legacy of financial stability and customer-focused insurance solutions 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
  • Chief Operating Officer - Kenneth Krieg
  • Chief Information Officer - Jim Frank
  • Regional Executive - Bob Bordeaux
  • Regional Executive - Timothy Zepnick
  • Regional Executive - Much Heare
  • Regional Executive - Paul Boehm
  • Regional Executive - Craig Simonson
  • 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. By overseeing the board of directors and executive management, Schuh ensures alignment between insurance product development and the evolving needs of policyholders. This leadership role involves maintaining the financial integrity of property and casualty lines while navigating complex regulatory environments. Dale Schuh drives the company toward sustainable growth by prioritizing risk management and capital allocation. Through consistent engagement with stakeholders, the Chair and Chief Executive Officer fosters a culture of accountability and excellence. By balancing the demands of homeowners, auto, and life insurance markets, Schuh secures the competitive position of the firm. Ultimately, the Chair and Chief Executive Officer maintains the foundational strength required to support the diverse insurance portfolio offered to clients nationwide.

    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, governs the mutual holding structure to ensure the long-term protection of policyholder interests. Overseeing the strategic direction of the holding company, McPartland manages the capital structure and investment strategies that support the broader insurance operations. This leadership role involves coordinating with the board to evaluate market opportunities and mitigate systemic risks within the property and casualty sectors. Pete McPartland drives organizational efficiency by aligning corporate governance with the specific requirements of a mutual insurance entity. By focusing on fiscal health and operational transparency, the Chairman and Chief Executive Officer, Sentry Mutual Holding Company strengthens the market presence of the firm. Through rigorous oversight of the holding company assets, McPartland ensures the continued delivery of reliable insurance products and annuities to a diverse customer base.
    Pete McPartland

    Kenneth Krieg - Chief Operating Officer

    Kenneth Krieg, the Chief Operating Officer at Sentry, manages the daily execution of insurance services and operational workflows across all product lines. Overseeing the claims administration and underwriting departments, Krieg ensures that service delivery meets the high standards expected by homeowners and auto insurance clients. This leadership role involves streamlining internal processes to reduce costs and improve the speed of policy issuance. Kenneth Krieg drives operational excellence by implementing lean methodologies and performance metrics that track the efficiency of the entire organization. By coordinating with regional executives, the Chief Operating Officer maintains consistency in service quality across diverse markets. Through the optimization of administrative functions, Krieg supports the financial objectives of the firm. Ultimately, the Chief Operating Officer ensures that the company remains agile and responsive to the changing demands of the property and casualty insurance industry.

    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 integration of data analytics and cybersecurity protocols, Frank ensures the secure processing of auto, homeowners, and life insurance policies. This leadership role involves modernizing legacy systems to improve customer service efficiency and internal data accessibility. Jim Frank drives innovation by implementing scalable cloud solutions that enhance the speed of claims processing and underwriting accuracy. By collaborating with other C-suite leaders, the Chief Information Officer aligns technology investments with the broader business goals of the organization. Through the deployment of advanced software tools, Frank optimizes the digital experience for policyholders. Ultimately, the Chief Information Officer maintains the technological resilience required to protect sensitive client information while supporting the company's growth in a competitive digital landscape.
    Jim Frank

    Bob Bordeaux - Regional Executive

    Bob Bordeaux, the Regional Executive at Sentry, directs business development and market expansion initiatives within the Eastern territory. Overseeing local agency relationships and distribution channels, Bordeaux ensures that property and casualty products reach target demographics effectively. This leadership role involves analyzing regional market trends to tailor insurance offerings to specific local needs. Bob Bordeaux drives revenue growth by fostering strong partnerships with independent agents and brokers. By monitoring regional performance metrics, the Regional Executive identifies opportunities for service improvement and market penetration. Through active engagement with local business communities, Bordeaux strengthens the brand presence of the firm. By managing the operational nuances of the Eastern market, the Regional Executive supports the broader corporate mission of providing reliable insurance coverage. Ultimately, Bordeaux ensures that regional strategies align with the overall growth objectives of the company.

    Timothy Zepnick - Regional Executive

    Timothy Zepnick, the Regional Executive at Sentry, manages the strategic deployment of insurance products and services throughout the Western region. Overseeing the operational performance of local teams, Zepnick ensures that homeowners and auto insurance solutions are delivered with high efficiency. This leadership role involves identifying regional risk factors and adjusting underwriting strategies to maintain profitability. Timothy Zepnick drives market share expansion by cultivating relationships with key distribution partners and local stakeholders. By analyzing regional data, the Regional Executive optimizes the allocation of resources to meet the specific demands of the Western market. Through consistent communication with corporate leadership, Zepnick ensures that regional activities support the overarching goals of the firm. By focusing on customer retention and service quality, the Regional Executive strengthens the competitive position of the company in the West. Ultimately, Zepnick secures long-term growth through disciplined regional management.

    Much Heare - Regional Executive

    Much Heare, the Regional Executive at Sentry, oversees the implementation of corporate insurance strategies within the Southern territory. Managing the relationships with regional agents and policyholders, Heare ensures that the company provides consistent and reliable property and casualty coverage. This leadership role involves assessing regional economic conditions to refine product positioning and sales tactics. Much Heare drives operational success by coordinating with internal departments to resolve regional service challenges and improve response times. By analyzing market feedback, the Regional Executive identifies new opportunities for product adoption and customer engagement. Through the effective management of regional resources, Heare supports the financial stability of the firm. By maintaining a focus on local market dynamics, the Regional Executive ensures that the company remains a preferred provider in the South. Ultimately, Heare contributes to the national growth of the organization through targeted regional execution.

    Paul Boehm - Regional Executive

    Paul Boehm, the Regional Executive at Sentry, directs the sales and service operations across the Northern region. Overseeing the performance of local insurance portfolios, Boehm ensures that homeowners, auto, and life insurance products meet the specific needs of the regional customer base. This leadership role involves managing relationships with distribution partners to maximize market reach and brand visibility. Paul Boehm drives growth by implementing regional marketing strategies that highlight the value of the company's insurance offerings. By monitoring regional competitive activity, the Regional Executive adjusts tactics to maintain a strong market position. Through the coordination of regional teams, Boehm ensures that service delivery remains efficient and customer-centric. By aligning regional objectives with corporate goals, the Regional Executive supports the overall financial health of the firm. Ultimately, Boehm secures the company's presence in the North through proactive management and strategic planning.

    Craig Simonson - Regional Executive

    Craig Simonson, the Regional Executive at Sentry, manages the operational and sales functions within the Central region. Overseeing the distribution of property and casualty insurance, Simonson ensures that the company maintains a strong presence in local markets. This leadership role involves analyzing regional risk profiles and collaborating with underwriting teams to ensure profitable growth. Craig Simonson drives business development by building and maintaining relationships with key agents and brokers. By focusing on regional service quality, the Regional Executive enhances customer satisfaction and retention rates. Through the effective use of regional data, Simonson identifies trends that inform future product development and sales strategies. By ensuring that regional operations align with corporate standards, the Regional Executive supports the long-term success of the firm. Ultimately, Simonson strengthens the company's market position in the Central region through disciplined execution and strategic oversight.

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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 Kenneth Krieg (Chief Operating 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), Kenneth Krieg (Chief Operating Officer) and other senior executives.
    How many executives does Sentry have?
    Sentry has 9 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, Chief Operating Officer, Chief Information Officer, Regional Executive.