Shepherd Insurance Executive and Leadership Team

July, 2026

Leadership Overview

Shepherd Insurance has 5 executives leading key functions including finance, operations, commercial lines, and employee benefits.

Driven by a commitment to comprehensive coverage, Shepherd Insurance provides Personal, Commercial, Employee, and Financial Insurance solutions, solidifying its market presence through strategic leadership and client-centric service.

Leadership Roles at Shepherd Insurance

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

    Steven Strigler, the Chief Financial Officer at Shepherd Insurance, directs the company's financial strategy and fiscal operations. Strigler oversees all aspects of financial planning, budgeting, and resource allocation, ensuring the company's long-term economic health and profitability. This leadership role involves managing investment portfolios, analyzing market trends, and mitigating financial risks to support the company's growth objectives. By optimizing financial processes and maintaining robust internal controls, Steven Strigler drives efficiency across all departments. The Chief Financial Officer's oversight extends to compliance with financial regulations and reporting standards, safeguarding the company's integrity and stakeholder trust. Strigler's expertise ensures Shepherd Insurance maintains a strong financial foundation to deliver its diverse insurance solutions.

    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, spearheads operational excellence across these key geographic markets. Del Medico directs the day-to-day management of regional business units, focusing on enhancing service delivery and operational efficiency. This executive role involves implementing strategic initiatives to expand market penetration and optimize resource utilization within Florida and Arizona. By fostering strong relationships with regional teams and stakeholders, Patrick Del Medico ensures seamless execution of company policies and objectives. The Chief Operating Officer of the Florida and Arizona Region. Partner's responsibilities include driving performance improvements, managing operational budgets, and ensuring compliance with regional regulations. Del Medico's leadership strengthens Shepherd Insurance's presence and service capabilities in these vital areas.

    Briggs Orsbon - President of Commercial Lines. Partner

    Briggs Orsbon, the President of Commercial Lines. Partner at Shepherd Insurance, leads the strategic direction and operational management of the commercial insurance division. Orsbon focuses on developing and executing strategies to expand market share and enhance product offerings for business clients. This leadership position involves overseeing underwriting, sales, and client relationship management for commercial policies. By identifying emerging market trends and client needs, Briggs Orsbon drives innovation in commercial insurance solutions. The President of Commercial Lines. Partner's role includes fostering strong partnerships with brokers and agents to ensure comprehensive client service. Orsbon's expertise in commercial risk assessment and management supports the company's mission to provide tailored insurance solutions. This focus ensures Shepherd Insurance effectively serves the diverse needs of its commercial clientele.
    Briggs Orsbon

    Stephen Gregory - President, Employee Benefits & Partner

    Stephen Gregory, the President, Employee Benefits & Partner at Shepherd Insurance, directs the strategic growth and operational oversight of the employee benefits division. Gregory spearheads the development and implementation of comprehensive employee benefits programs designed to meet the evolving needs of businesses and their workforces. This executive function involves managing client relationships, expanding service offerings, and ensuring the delivery of high-quality benefits administration. By cultivating strategic alliances with benefit providers and employers, Stephen Gregory enhances the value proposition for clients. The President, Employee Benefits & Partner's responsibilities include driving innovation in benefits consulting and ensuring regulatory compliance. Gregory's leadership ensures Shepherd Insurance provides robust and competitive employee benefit solutions, supporting organizational well-being and talent retention.

    Matt Kleymeyer - President, Employee Benefits

    Matt Kleymeyer, the President, Employee Benefits at Shepherd Insurance, drives the strategic vision and operational execution for the employee benefits sector. Kleymeyer focuses on expanding the portfolio of employee benefits solutions, ensuring they align with current market demands and client objectives. This role involves leading the team responsible for benefits consulting, plan design, and ongoing client support. By analyzing industry trends and client feedback, Matt Kleymeyer identifies opportunities for service enhancement and product development. The President, Employee Benefits's oversight ensures the seamless delivery of tailored benefits packages, contributing to client satisfaction and retention. Kleymeyer's commitment to excellence supports Shepherd Insurance's mission to provide comprehensive financial and insurance solutions for employers and their employees.

    Explore Leadership Teams in Insurance

    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 Briggs Orsbon (President of Commercial Lines. 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), Briggs Orsbon (President of Commercial Lines. 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, Chief Operating Officer of the Florida and Arizona Region. Partner, President of Commercial Lines. Partner, President, Employee Benefits & Partner, President, Employee Benefits.