Spotlight On: Ken Thompson, Senior Vice President & Senior Trust Executive, Jacksonville, Cypress Bank & Trust
Key points:
- • Cypress Bank & Trust exceeded its growth goals in Jacksonville this past year.
- • Jacksonville’s growth is driving steady demand for trust and fiduciary services.
- • The bank aims to double its Jacksonville operation over the next five years.
November 2026 — In an interview with Invest:, Ken Thompson, senior vice president and senior trust executive at Cypress Bank & Trust in Jacksonville, discussed the bank’s continued growth, the increasing need for relationship-based wealth management, and the importance of empathy in fiduciary services. “You have to care about the people you work for, and the people you work with,” Thompson said.
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How has the past year been for Cypress Bank & Trust, and what does it say about the wealth management and trust services environment?
This past year has been one of continued growth. We exceeded our goals and expectations, added new people to the office, and strengthened our position in the market.
Cypress provides traditional fiduciary investment management, trust and estate administration, along with full-service retail banking. Jacksonville has performed particularly well on the trust and investment side, while our banking operation continues to grow. Five years ago, we had just received our bank charter and were starting from scratch. Today we have two commercial bankers and additional support staff, and there is still plenty of opportunity ahead. Jacksonville and North Florida remain strong markets for us.
What are you seeing among clients preparing for succession planning, leadership transitions, or liquidity events?
Jacksonville continues to attract growth, but there are also many established businesses preparing for transitions. We like to be involved in those conversations from both the commercial banking and fiduciary perspectives.
There are financial decisions to make, but there are also family dynamics and personal adjustments that come with a liquidity event. Our role is to help clients work through both. We coordinate with attorneys, tax advisers, insurance professionals, and others so clients have the right team in place. Bringing those perspectives together helps people reach sound decisions and gives them confidence throughout the process.
What helps build and maintain trust in long-term client relationships?
I interview a lot of people, and one question I hear often is what it takes to succeed in this business. Technical knowledge is expected. People need to understand investments, finance, legal issues, and the mechanics of the work. But the truly successful people have empathy. You have to care about the people you work for and the people you work with.
If you come to work every day with that mindset, you’re going to be successful. The people who do this best can listen to clients, understand even what they are not saying, and help find solutions. If they cannot solve the issue themselves, they bring in someone who can.
That philosophy reflects our organization. We begin by asking clients about their business, their goals, their challenges, and their risks. Once we understand who they are, we can recommend solutions that fit their circumstances instead of leading with a predetermined answer.
How are digital tools enhancing the client experience while allowing you to maintain a personal approach?
Technology has to support relationships rather than replace them.
Since we last spoke, we upgraded our trust and investment platform to a more flexible system that improves both our internal processes and the client experience. Clients can access information more easily, while our teams operate more efficiently.
The objective is to spend less time on administrative work and more time building relationships. We want to know our clients well enough that we become part of their family’s story, celebrating milestones and understanding their long-term goals. Those lasting relationships are what define successful trust and fiduciary work.
How has Florida’s continued population growth affected demand for trust and fiduciary services?
We continue to see tremendous support from the professional community. Many of our first conversations begin with clients deciding who should serve as trustee or handle their affairs if they become incapacitated or after they are gone. They often do not want to place that responsibility on family members or may not have family nearby.
We are having those conversations with new clients almost every week. They take time because you need to understand each family’s circumstances, including their children, family dynamics, and long-term goals. That understanding allows us to recommend the right planning structures. Jacksonville’s continued growth has created strong demand for those services, and our local approach has positioned us well to meet it.
What trends are you seeing in charitable planning and legacy-building strategies?
Charitable planning is something I care deeply about. Giving back to the community has always been important to me, and it is also becoming an increasingly valuable planning tool.
After many years serving on the Planned Giving Council, I have developed relationships with many nonprofit organizations. Those connections help us introduce clients to opportunities that align with both their personal goals and their financial planning.
As tax rules continue to evolve, charitable planning has become a more common part of conversations. We do not pretend to have every answer ourselves. Instead, we work with a network of professionals to help clients find solutions that benefit both their families and the organizations they care about.
What is your outlook for Cypress Bank & Trust over the next five years?
Our top priority is continuing to grow the banking side of our Jacksonville operation. We have expanded significantly since launching here five years ago, and we are continuing to invest in people who will help grow both the bank and the broader organization.
Jacksonville remains an attractive market, and while competition is strong, we believe our relationship-driven approach sets us apart. We have intentionally focused on providing a personalized experience rather than trying to be everything to everyone.
Looking ahead, I would like to see us expand our presence, continue adding talented people, and ultimately double the size of our Jacksonville operation over the next five years.
Want more? Read the Invest: Jacksonville report.
