Shepherd Insurance Executive and Leadership Team

June, 2026

Leadership Overview

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

Driven by a commitment to comprehensive client service, Shepherd Insurance delivers tailored personal, commercial, employee, and financial insurance solutions, solidifying its market presence through strategic leadership and a client-centric operational philosophy.

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
  • Founder & President - Adam Besnard
  • Steven Strigler - Chief Financial Officer

    Steven Strigler, the Chief Financial Officer at Shepherd Insurance, directs all financial planning, accounting operations, and fiscal strategy. Strigler manages the company's capital structure, investment activities, and risk management functions, ensuring robust financial health and compliance with regulatory standards. This leadership role involves optimizing resource allocation across all business units, including personal, commercial, employee, and financial insurance sectors. By meticulously analyzing financial data, Steven Strigler drives profitability and supports sustainable growth initiatives. The Chief Financial Officer's oversight extends to budgeting, forecasting, and reporting, providing critical insights for executive decision-making and maintaining investor confidence. Strigler's financial acumen underpins the company's ability to navigate market fluctuations and capitalize on emerging opportunities within the insurance landscape.

    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 execution and strategic development across these key geographic markets. Del Medico oversees all day-to-day business activities, ensuring seamless service delivery for personal, commercial, employee, and financial insurance products. This executive's responsibilities include optimizing operational efficiency, managing regional teams, and fostering a culture of high performance. Patrick Del Medico drives market penetration and client retention strategies specific to the unique demands of the Florida and Arizona markets. The Chief Operating Officer of the Florida and Arizona Region. Partner's role involves close collaboration with sales and underwriting departments to align operational capabilities with market opportunities, thereby enhancing the company's regional footprint and overall service excellence. Del Medico's leadership ensures consistent application of company standards and drives regional growth.

    Briggs Orsbon - President of Commercial Lines. Partner

    Briggs Orsbon, the President of Commercial Lines. Partner at Shepherd Insurance, directs the strategic vision and operational management for all commercial insurance offerings. Orsbon focuses on expanding market share and enhancing product development within the commercial sector, serving businesses of all sizes. This leadership position involves cultivating strong relationships with brokers, underwriters, and corporate clients to deliver tailored risk management solutions. Briggs Orsbon drives innovation in commercial insurance products, ensuring they meet evolving industry needs and regulatory requirements. The President of Commercial Lines. Partner's oversight includes managing the commercial sales force, underwriting teams, and claims handling processes to ensure superior client service and profitability. Orsbon's expertise in commercial risk assessment and strategic market positioning strengthens Shepherd Insurance's competitive edge in this vital segment.
    Briggs Orsbon

    Stephen Gregory - President, Employee Benefits & Partner

    Stephen Gregory, the President, Employee Benefits & Partner at Shepherd Insurance, leads the strategic direction and operational execution of the employee benefits division. Gregory focuses on developing and delivering comprehensive benefits packages, including health, dental, vision, and retirement plans, to corporate clients. This executive's role involves managing client relationships, identifying market trends, and innovating benefit solutions to attract and retain talent for employers. Stephen Gregory oversees a dedicated team of benefits specialists, ensuring expert guidance and support for clients navigating complex benefit landscapes. The President, Employee Benefits & Partner's responsibilities extend to fostering strategic partnerships with insurance carriers and benefit providers to offer competitive and compliant offerings. Gregory's leadership ensures Shepherd Insurance remains a trusted advisor for businesses seeking robust employee benefit programs.

    Adam Besnard - Founder & President

    Adam Besnard, the Founder & President at Shepherd Insurance, established the company with a vision for providing comprehensive insurance solutions. Besnard guides the overall strategic direction and corporate culture, ensuring alignment with the company's mission to serve personal, commercial, employee, and financial insurance needs. This foundational role involves fostering innovation, driving growth across all business lines, and maintaining the company's commitment to client satisfaction and integrity. Adam Besnard actively engages with key stakeholders, including clients, partners, and employees, to uphold the company's values and expand its market reach. The Founder & President's leadership ensures that Shepherd Insurance consistently delivers exceptional service and adapts to the dynamic insurance industry landscape, solidifying its reputation as a trusted provider.

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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 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, Founder & President.