Shepherd Insurance Executive and Leadership Team

July, 2026

Leadership Overview

Shepherd Insurance has 4 executives leading key functions including finance, operations, employee benefits, and commercial lines.

Driven by a commitment to comprehensive coverage, Shepherd Insurance provides Personal, Commercial, Employee, and Financial Insurance solutions, solidifying its market presence from its Carmel, Indiana headquarters.

Leadership Roles at Shepherd Insurance

  • Chief Financial Officer - Steven Strigler
  • Chief Operating Officer of the Florida and Arizona Region. Partner - Patrick Del Medico
  • President, Employee Benefits & Partner - Stephen Gregory
  • President of Commercial Lines. Partner - Briggs Orsbon
  • Steven Strigler - Chief Financial Officer

    Steven Strigler, the Chief Financial Officer at Shepherd Insurance, directs all financial strategy and fiscal operations. Overseeing the company's financial health, the Chief Financial Officer ensures robust capital management and drives profitability across all business segments. This leadership position involves rigorous budget oversight, investment analysis, and the development of long-term financial forecasts critical for sustained growth. By optimizing resource allocation and managing risk, Steven Strigler directly supports the company's mission to deliver comprehensive insurance solutions. The Chief Financial Officer's expertise is vital for maintaining financial stability and expanding market reach within the insurance sector.

    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, executes operational strategies across key geographic markets. Overseeing daily business functions in Florida and Arizona, the Chief Operating Officer ensures seamless service delivery and operational efficiency. This role involves managing regional teams, optimizing workflows, and driving performance metrics to align with corporate objectives. By focusing on regional growth and client satisfaction, Patrick Del Medico directly contributes to Shepherd Insurance's expansion and market penetration. The Chief Operating Officer's leadership is essential for maintaining high service standards and achieving operational excellence within these specific territories.

    Stephen Gregory - President, Employee Benefits & Partner

    Stephen Gregory, the President, Employee Benefits & Partner at Shepherd Insurance, leads the strategic direction and operational execution of employee benefits programs. Overseeing the development and delivery of comprehensive benefits solutions, the President, Employee Benefits ensures client needs are met with tailored offerings. This critical role involves managing relationships with employers, navigating complex regulatory landscapes, and driving innovation in benefits design. By fostering strong client partnerships and enhancing service offerings, Stephen Gregory directly supports the company's commitment to providing robust financial and employee insurance solutions. The President, Employee Benefits' focus on specialized market segments strengthens Shepherd Insurance's overall value proposition.

    Briggs Orsbon - President of Commercial Lines. Partner

    Briggs Orsbon, the President of Commercial Lines. Partner at Shepherd Insurance, directs the strategy and growth initiatives for the commercial insurance division. Overseeing all aspects of commercial client acquisition and retention, the President of Commercial Lines ensures the delivery of specialized insurance products. This leadership position involves managing underwriting teams, developing market penetration strategies, and fostering key broker relationships. By driving revenue growth and expanding market share within the commercial sector, Briggs Orsbon directly enhances Shepherd Insurance's comprehensive service portfolio. The President of Commercial Lines' expertise is fundamental to securing and serving business clients effectively.
    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 Patrick Del Medico (Chief Operating Officer of the Florida and Arizona Region. Partner) and Stephen Gregory (President, Employee Benefits & 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), Patrick Del Medico (Chief Operating Officer of the Florida and Arizona Region. Partner), Stephen Gregory (President, Employee Benefits & Partner) and other senior executives.
    How many executives does Shepherd Insurance have?
    Shepherd Insurance has 4 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, Chief Operating Officer of the Florida and Arizona Region. Partner, President, Employee Benefits & Partner, President of Commercial Lines. Partner.