Leadership Team

Dudley D. Wooley
Independent Director
Dudley D. Wooley is Chief Executive Officer of Ross & Yerger Insurance, Inc., a super-regional, employee-owned independent insurance agency headquartered in Jackson, Mississippi. With more than three decades at the firm, he has played a central role in shaping its growth, leadership, and long-term strategic direction. He was promoted to CEO/COO in 2013 and has served as CEO since 2025, with responsibility for overall leadership and performance of the organization.
Previously, Mr. Wooley served as President and Chief Operating Officer, where he led agency growth and profitability initiatives, developed the firm’s perpetuation strategy, and supported its sales and management teams. Earlier in his career, he served as an Account Executive and Vice President, overseeing commercial, personal, and group benefit accounts, with a focus on nonprofit and healthcare clients.
In addition to his executive role, Mr. Wooley serves as a Trustee of the Jones Family Trusts, helping oversee a diversified portfolio of assets across public equities, private equity, real estate, oil and gas, and fixed income investments on behalf of approximately 170 beneficiaries.
He began his career with Andersen Consulting (now Accenture) and later worked at Marketing Research Institute, where he developed experience in consulting, analytics, and client advisory.
Mr. Wooley holds an MBA from Millsaps College and a Bachelor of Science in Mathematics from Vanderbilt University. He is a Chartered Property Casualty Underwriter (CPCU), Certified Risk Manager (CRM), Certified Insurance Counselor (CIC), and Accredited Adviser in Insurance (AAI). He has held numerous leadership roles in industry and community organizations and has been actively involved in nonprofit, healthcare, and educational institutions throughout his career.
