Shepard Ottaway Relationship Manager

Shepard brings both professional experience and personal dedication to his role at Maplewood Investments, where he helps financial professionals and investors pursue financial goals with confidence and clarity. His personal and professional background blends athletics, leadership, and finance, experience that naturally motivates him to approach each relationship with discipline, focus, and a commitment to long-term success.

Before joining the firm in 2026, Shepard built a strong foundation in how to support individuals and families with their insurance and retirement planning needs at Western & Southern Life. In 2021, he continued his career as a financial advisor at Midtown Financial Advisors, expanding his ability to serve clients with tailored strategies and solutions.

Shepard earned a bachelor’s degree in business management while competing on the track team all four years at Wingate University.

He holds Series 6, 63, and 65 securities licenses, and his experience in both the registered investment advisory and broker-dealer sides of the financial industry further enriches the perspective he brings to his clients and the Maplewood Investments team.

Outside the office, Shepard invests his time in developing the next generation as a high school track and field coach at High Point Christian Academy. A former athlete himself, he was part of two North Carolina state championship teams in high school, earned a silver medal in a collegiate relay event, and still enjoys competing in invitational meets a few times each year. He also serves as a deacon at Life Community Church, where faith and service remain central to his life.