Leadership Overview
Shepherd Insurance has 5 executives leading key functions including financial strategy, regional operations, commercial lines, and employee benefits.
Focused on comprehensive risk management, Shepherd Insurance delivers tailored personal, commercial, and financial insurance solutions while maintaining a commitment to client-centric service and long-term stability across diverse market sectors.
Focused on comprehensive risk management, Shepherd Insurance delivers tailored personal, commercial, and financial insurance solutions while maintaining a commitment to client-centric service and long-term stability across diverse market sectors.
Leadership Roles at Shepherd Insurance
Steven Strigler - Chief Financial Officer
Steven Strigler, the Chief Financial Officer at Shepherd Insurance, directs all fiscal planning and capital allocation strategies. Overseeing the financial health of the organization, the Chief Financial Officer ensures rigorous compliance with industry standards while optimizing investment portfolios for long-term growth. This leadership role involves managing complex budgetary frameworks and providing data-driven insights to the executive board to support sustainable expansion. By streamlining internal accounting processes, Steven Strigler directly impacts the operational efficiency of the firm. Strigler maintains a focus on risk mitigation, ensuring the company remains resilient against market volatility. Through precise financial modeling and strategic resource management, the Chief Financial Officer secures the necessary capital to fund new insurance product development. Ultimately, Strigler drives the fiscal discipline required to maintain the competitive market position of the firm within the broader 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, directs all operational activities across these critical southern and western markets. Overseeing regional service delivery, the Chief Operating Officer of the Florida and Arizona Region. Partner ensures that local client needs align with the broader corporate mission of providing comprehensive insurance solutions. This leadership role involves scaling regional infrastructure and managing high-level partnerships to capture market share in competitive territories. By optimizing workflows and enhancing service quality, Patrick Del Medico directly impacts the growth trajectory of the firm in these specific geographies. Del Medico maintains a focus on operational excellence, ensuring that regional teams execute strategies with precision and agility. Through effective management of regional resources, the Chief Operating Officer of the Florida and Arizona Region. Partner supports the overall expansion goals of the company.
Briggs Orsbon - President of Commercial Lines. Partner
Briggs Orsbon, the President of Commercial Lines. Partner at Shepherd Insurance, directs the strategy and growth of the commercial insurance division. Overseeing the development of complex risk management products, the President of Commercial Lines. Partner ensures that business clients receive tailored coverage solutions that address specific industry vulnerabilities. This leadership role involves collaborating with underwriters and sales teams to expand the commercial portfolio across diverse sectors. By refining product offerings and enhancing client engagement, Briggs Orsbon directly impacts the revenue generation of the firm. Orsbon maintains a focus on market trends, ensuring that commercial solutions remain relevant in an evolving economic environment. Through strategic oversight of the commercial lines department, the President of Commercial Lines. Partner drives the acquisition of new enterprise accounts. Ultimately, Orsbon secures the long-term profitability of the commercial division by fostering strong relationships with key stakeholders and industry partners.
Matt Kleymeyer - President, Employee Benefits
Matt Kleymeyer, the President, Employee Benefits at Shepherd Insurance, directs the design and implementation of comprehensive benefit programs for corporate clients. Overseeing the employee benefits division, the President, Employee Benefits ensures that organizations provide competitive health and financial security packages to their workforces. This leadership role involves navigating complex regulatory environments and negotiating with carriers to deliver cost-effective solutions. By analyzing workforce demographics and health trends, Matt Kleymeyer directly impacts the retention and satisfaction rates of client companies. Kleymeyer maintains a focus on innovation, ensuring that benefit offerings include modern wellness and financial planning tools. Through strategic management of the benefits portfolio, the President, Employee Benefits supports the growth of the firm by attracting large-scale corporate accounts. Ultimately, Kleymeyer drives the success of the benefits department by aligning service delivery with the evolving needs of modern employers and their staff.
Stephen Gregory - President, Employee Benefits & Partner
Stephen Gregory, the President, Employee Benefits & Partner at Shepherd Insurance, directs the strategic vision and partnership initiatives within the employee benefits sector. Overseeing high-level client relationships, the President, Employee Benefits & Partner ensures that the firm maintains a dominant presence in the benefits consulting market. This leadership role involves architecting long-term growth strategies and identifying new opportunities for service expansion. By fostering collaborative efforts with other executive leaders, Stephen Gregory directly impacts the overall market influence of the company. Gregory maintains a focus on operational scalability, ensuring that the benefits division can handle increasing demand while maintaining high service standards. Through the cultivation of strategic partnerships, the President, Employee Benefits & Partner strengthens the competitive advantage of the firm. Ultimately, Gregory drives the expansion of the benefits practice by leveraging deep industry expertise and a commitment to delivering superior value to corporate clients.
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