Kassi O’Brien

Vice President – Branch Leader (Hampton Roads)

Kassi O’Brien was named Branch Leader of Scott Insurance’s Hampton Roads office following the opening of the location in 2025. In this role, she leads Scott’s efforts to serve employers throughout the Hampton Roads region while helping advance the company’s strategic growth and commitment to building strong client and community relationships.

As a Vice President and Benefits Consultant, Kassi partners with employers to develop innovative employee benefits strategies that support workforce well-being while managing the financial risks associated with healthcare. She brings a unique blend of operational, financial, and consulting expertise to her work, helping organizations evaluate plan performance, implement data-driven solutions, and design competitive benefits programs that attract and retain talent. Her areas of expertise include self-funding strategies, pharmacy benefit optimization, group captives, and long-term benefits planning.

Prior to joining Scott Insurance, Kassi worked as a Benefits Consultant for an independent benefits firm, advising clients on employee benefit plan design and strategy. She began her career as an industrial engineer in manufacturing, leading teams focused on operational efficiency and quality improvement before transitioning into cost accounting and financial performance management.

Kassi is active in several professional and community organizations, serving on the Executive Committee of the Mid-Atlantic Chapter of The ESOP Association and on the boards of Hampton Roads SHRM, the Independent Insurance Agents of Virginia, Junior Achievement of Central Virginia, and Junior Achievement of Greater Hampton Roads. She earned a Bachelor of Science in Economics from Converse College and a Master of Business Administration from Clemson University. She is also a Dale Carnegie graduate and holds Six Sigma and Supply Chain Management certifications.