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.
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
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.

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.
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