Shepherd Insurance Executive and Leadership Team

Steven Strigler, the Chief Financial Officer at Shepherd Insurance, manages all fiscal operations and capital allocation strategies. Overseeing the financial health of the organization, the Chief Financial Officer directs budgeting processes and long-term investment planning to support the delivery of Personal, Commercial, Employee and Financial Insurance solutions. This leadership role involves rigorous analysis of market trends to optimize profitability and ensure the firm maintains a competitive edge in the insurance industry. By implementing advanced financial modeling, Steven Strigler strengthens the balance sheet and provides the necessary resources for sustainable growth. The Chief Financial Officer collaborates closely with the executive team to align fiscal objectives with the broader corporate mission. Through disciplined oversight of assets and liabilities, the Chief Financial Officer secures the financial foundation required for the company to expand its reach and continue providing high-quality coverage to diverse client bases across the United States.

Patrick Del Medico, the Chief Operating Officer of the Florida and Arizona Region. Partner at Shepherd Insurance, directs all operational activities within these critical growth markets. Overseeing regional service delivery, the Chief Operating Officer of the Florida and Arizona Region. Partner ensures that Personal, Commercial, Employee and Financial Insurance solutions meet the specific needs of clients in these areas. This leadership role involves streamlining workflows and enhancing operational efficiency to support rapid expansion. By coordinating with local teams, Patrick Del Medico drives the execution of regional business strategies and maintains high standards of service excellence. The Chief Operating Officer of the Florida and Arizona Region. Partner monitors performance metrics to ensure alignment with the overarching corporate goals. Through proactive management of regional resources, the Chief Operating Officer of the Florida and Arizona Region. Partner fosters a culture of accountability and operational agility, directly contributing to the firm's success in these key geographic territories.

Matt Kleymeyer, the President, Employee Benefits at Shepherd Insurance, architects the strategic direction for all employee benefit programs. Overseeing the design and implementation of comprehensive health and wellness packages, the President, Employee Benefits ensures that corporate clients receive tailored solutions that enhance workforce retention and satisfaction. This leadership role involves navigating complex regulatory landscapes and negotiating with carriers to secure optimal coverage terms. By analyzing market data, Matt Kleymeyer identifies emerging trends in the benefits sector and integrates these insights into the company's service offerings. The President, Employee Benefits collaborates with other senior leaders to ensure that benefit strategies align with the broader financial and commercial goals of the firm. Through the development of innovative service models, the President, Employee Benefits drives client engagement and strengthens the company's market position as a premier provider of employee-focused insurance solutions across the national landscape.

Briggs Orsbon, the President of Commercial Lines. Partner at Shepherd Insurance, directs the strategy and growth of the commercial insurance division. Overseeing the underwriting and risk assessment processes, the President of Commercial Lines. Partner ensures that the firm provides robust protection for businesses against complex operational risks. This leadership role involves managing relationships with major carriers and developing specialized insurance products that address the evolving needs of commercial clients. By leveraging deep industry expertise, Briggs Orsbon optimizes the commercial portfolio and drives revenue growth through targeted market penetration. The President of Commercial Lines. Partner works in tandem with the executive team to ensure that commercial offerings remain competitive and aligned with the company's overall mission. Through the implementation of rigorous risk management standards, the President of Commercial Lines. Partner maintains the integrity of the commercial book of business and supports the firm's reputation for excellence in the insurance sector.

Stephen Gregory, the President, Employee Benefits & Partner at Shepherd Insurance, focuses on the expansion and optimization of the employee benefits division. Overseeing client acquisition and retention strategies, the President, Employee Benefits & Partner ensures that the firm delivers high-value consulting services that help businesses manage their human capital costs effectively. This leadership role involves building strong partnerships with employers and providing strategic guidance on benefit plan design and administration. By fostering a culture of innovation, Stephen Gregory drives the adoption of new technology platforms that simplify the benefits experience for clients. The President, Employee Benefits & Partner collaborates with the broader leadership team to ensure that the benefits division contributes significantly to the company's overall financial performance. Through a commitment to service excellence and deep industry knowledge, the President, Employee Benefits & Partner strengthens the firm's competitive advantage and supports the long-term success of clients across the diverse markets served.