Jackson Shaw

Jackson Shaw, MBA

Trust Officer 

As a Trust Officer with Caldwell Trust Company in Sarasota, Florida, Jackson Shaw brings a strong foundation in trust administration, wealth management, investment planning, and client relationships. Recently promoted from Trust Associate, he has quickly distinguished himself through his ability to work directly with clients, collaborate with senior trust professionals, and navigate the complexities of managing wealth across generations.

In his current role, Jackson’s experience encompasses trust and estate administration, investment management, retirement planning, IRA distributions and required minimum distributions, charitable giving strategies, bill pay, asset transfers, and client account administration. He also works with specialized assets and structures, including real estate and Irrevocable Life Insurance Trusts (ILITs).

Prior to becoming a Trust Officer, Jackson supported Caldwell’s Trust Officers in the administration and management of client relationships. His responsibilities provided him with broad exposure to estate planning, trust and legal documents, investment strategy, regulatory requirements, and the many administrative details involved in serving high-net-worth families. He has also participated in Caldwell’s investment, real estate,
discretionary, and trust committees, gaining valuable insight into the decision-making that supports clients’ long-term financial and estate-planning goals.

What sets Jackson apart is his genuine interest in the people behind the portfolios. He has experience meeting with prospective and existing clients, centers of influence, and professional advisors, and he enjoys helping clients make thoughtful decisions during periods of uncertainty—including navigating concerns surrounding market volatility and changing economic and political environments.

His path into the trust industry began at Campbell University, where he gained experience through the Trust and Wealth Management program and served as a graduate assistant within the Lundy-Fetterman School of Business. He also gained valuable industry experience through internships with Caldwell Trust Company and Wells Fargo.

Early in his career, Jackson has already developed a perspective that goes beyond numbers: effective wealth management is ultimately about understanding people, protecting what they have built, and helping families plan confidently for what comes next.

Outside of his professional career, Jackson holds a Private Pilot’s License, reflecting the same curiosity,  discipline, and commitment to continuous learning that he brings to his work in the trust and wealth management industry.