Jonathan Mason Askew

Jonathan Mason Askew, MBA

Trust Officer 

Jonathan Mason Askew, MBA, is a Trust Officer with Caldwell Trust Company, where he works with clients and families on trust and estate administration, investment portfolio management, relationship development, and business development. Based in Sarasota and Venice, Florida, Mason brings a strong foundation in wealth management, financial planning, and fiduciary services to his work with clients.

Mason earned a Bachelor of Business Administration in Trust and Wealth Management from Campbell University, where he graduated with a 3.86 cumulative GPA and completed the university’s 4+1 MBA program. He also earned a minor in Financial Planning. Prior to Campbell, Mason studied Professional Pilot- Aviation at the University of Oklahoma, developing an early interest in aviation and disciplined, detail-oriented professional environments. He completed up to a solo flight with 30 hours and was certified via the FAA ground school before departing for Campbell University to pursue his collegiate
athletics career.

During his collegiate career, Mason was an NCAA Division I track and field athlete specializing in pole vault at Campbell University. He was part of the program that earned the school’s first conference championship in 2022. He also served as Vice President of Kappa Sigma’s Sigma Phi Chapter, where he oversaw risk management and academics.
Before joining Caldwell Trust Company full time, Mason gained experience through internships with both Caldwell Trust Company and Cumberland Trust Company in Nashville. His experience includes trust and estate administration, portfolio management, IRA investment proposals, compliance and risk review, special assets, discretionary distributions, and estate administration. He has also participated in investment, compliance, administration, and development committees, giving him broad exposure to
the operational and fiduciary responsibilities of the trust industry.

In addition to his professional responsibilities, Mason is committed to serving his community. He  currently serves as a Board Trustee of the Pines of Sarasota Foundation and is active on its Investment, Finance, and Communication committees. He is passionate about supporting organizations and initiatives that strengthen the Sarasota community.

Outside of work, Mason enjoys hunting, fishing, and other outdoor activities, as well as playing guitar, producing music, staying active, and participating in community recreational leagues and events. His diverse interests, combined with his academic and professional background, reflect his commitment to continuous growth, service, and building lasting relationships with clients and the community.