Shepherd Insurance Executive and Leadership Team

October, 2026

Leadership Overview

Shepherd Insurance has 5 executives leading key functions including financial oversight, operational management, regional expansion, employee benefits, and commercial lines.

Committed to comprehensive risk management, Shepherd Insurance delivers tailored personal, commercial, and financial insurance solutions while maintaining a strong focus on client-centric protection and long-term stability.

Leadership Roles at Shepherd Insurance

  • Chief Financial Officer - Steven Strigler
  • Partner. Chief Operating Officer - Pete Harrington
  • Chief Operating Officer of the Florida and Arizona Region. Partner - Patrick Del Medico
  • President, Employee Benefits - Matt Kleymeyer
  • President of Commercial Lines. Partner - Briggs Orsbon
  • Steven Strigler - Chief Financial Officer

    Steven Strigler, the Chief Financial Officer at Shepherd Insurance, manages the entire fiscal architecture of the organization. Overseeing capital allocation, financial reporting, and long-term investment strategies, the Chief Financial Officer ensures the firm maintains robust liquidity to support diverse insurance portfolios. This leadership role involves rigorous analysis of market trends to optimize profitability across personal and commercial sectors. By directing internal audits and fiscal compliance, Steven Strigler strengthens the overall economic health of the enterprise. The Chief Financial Officer collaborates with the Board to align budgetary goals with the broader mission of providing reliable financial protection. Through precise management of assets and liabilities, Strigler secures the fiscal foundation necessary for sustained growth. This executive oversight remains critical for navigating complex regulatory environments while maximizing value for all stakeholders involved in the company's expansive insurance operations.

    Pete Harrington - Partner. Chief Operating Officer

    Pete Harrington, the Partner. Chief Operating Officer at Shepherd Insurance, directs the daily operational workflows that sustain the company's service delivery. Overseeing internal processes, technology integration, and organizational efficiency, the Partner. Chief Operating Officer ensures seamless coordination between departments to support the firm's diverse insurance offerings. This leadership role involves refining operational protocols to enhance client experiences across personal and commercial lines. By implementing scalable systems, Pete Harrington drives productivity and maintains high standards of service excellence. The Partner. Chief Operating Officer works closely with other executive leaders to synchronize business objectives with operational capabilities. Through constant evaluation of performance metrics, Harrington optimizes resource utilization and supports the company's commitment to providing comprehensive insurance solutions. This focus on operational excellence remains vital for maintaining the competitive edge of the firm within the broader insurance marketplace.

    Patrick Del Medico - Chief Operating Officer of the Florida and Arizona Region. Partner

    Patrick Del Medico, the Chief Operating Officer of the Florida and Arizona Region. Partner at Shepherd Insurance, directs all strategic operations across these key geographic markets. Overseeing regional growth initiatives, local client acquisition, and service delivery, the Chief Operating Officer of the Florida and Arizona Region. Partner ensures that the company's insurance solutions meet the specific needs of these diverse territories. This leadership role involves managing regional teams and fostering strong relationships with local partners to expand market presence. By tailoring operational strategies to the unique demands of the Florida and Arizona markets, Patrick Del Medico drives significant revenue growth and brand recognition. The Chief Operating Officer of the Florida and Arizona Region. Partner collaborates with corporate leadership to ensure regional activities align with the overarching mission of the firm. Through dedicated regional oversight, Del Medico secures a dominant position for the company in these critical areas.

    Matt Kleymeyer - President, Employee Benefits

    Matt Kleymeyer, the President, Employee Benefits at Shepherd Insurance, directs the development and distribution of comprehensive benefit programs for corporate clients. Overseeing product design, carrier relations, and client consulting, the President, Employee Benefits ensures that organizations receive tailored solutions for workforce protection. This leadership role involves analyzing market shifts in healthcare and retirement planning to provide competitive advantages for employers. By architecting innovative benefit strategies, Matt Kleymeyer drives client retention and attracts new business across the national landscape. The President, Employee Benefits works in tandem with the commercial lines division to provide holistic risk management for corporate entities. Through constant engagement with industry experts and stakeholders, Kleymeyer maintains the firm's reputation for excellence in the employee benefits sector. This strategic focus on human capital solutions remains essential for the company's mission to provide robust financial and insurance support to businesses.
    Matt Kleymeyer

    Briggs Orsbon - President of Commercial Lines. Partner

    Briggs Orsbon, the President of Commercial Lines. Partner at Shepherd Insurance, directs the strategy and execution of all commercial insurance products. Overseeing underwriting standards, risk assessment, and portfolio management, the President of Commercial Lines. Partner ensures that businesses receive tailored coverage for complex operational risks. This leadership role involves managing relationships with major carriers and developing specialized insurance programs for diverse industries. By driving growth in the commercial sector, Briggs Orsbon strengthens the firm's market position and revenue streams. The President of Commercial Lines. Partner collaborates with the executive team to align commercial offerings with the evolving needs of the business community. Through rigorous analysis of industry-specific risks, Orsbon provides the necessary protection for corporate clients to thrive. This focus on commercial excellence remains a cornerstone of the company's commitment to providing comprehensive insurance solutions across the United States.
    Briggs Orsbon

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    Frequently Asked Questions Regarding Shepherd Insurance Top Executives and Leadership Team

    Who leads Shepherd Insurance?
    Shepherd Insurance is led by Steven Strigler (Chief Financial Officer), along with executives such as Pete Harrington (Partner. Chief Operating Officer) and Patrick Del Medico (Chief Operating Officer of the Florida and Arizona Region. Partner).
    Who is part of Shepherd Insurance’s executive team?
    The executive team of Shepherd Insurance includes leaders such as Steven Strigler (Chief Financial Officer), Pete Harrington (Partner. Chief Operating Officer), Patrick Del Medico (Chief Operating Officer of the Florida and Arizona Region. Partner) and other senior executives.
    How many executives does Shepherd Insurance have?
    Shepherd Insurance has 5 executives leading key business areas.
    What roles are included in Shepherd Insurance’s leadership team?
    The leadership team of Shepherd Insurance includes roles such as Chief Financial Officer, Partner. Chief Operating Officer, Chief Operating Officer of the Florida and Arizona Region. Partner, President, Employee Benefits, President of Commercial Lines. Partner.