As a Wealth Management Consultant at Cheetah, Jerry Gillespie helps clients get more from the software they use every day. His work requires a broad understanding of the platform and the operational challenges trust and wealth management professionals face.
That experience also shapes Jerry’s role at the Hunt, Cheetah’s annual client conference. After attending the conference three times, he has seen how practical training, peer conversations, and new professional connections can help attendees return to work with fresh and exciting ideas.
We recently sat down with Jerry to learn more about his role at the Hunt, what he has learned from attendees, and what first-time participants can expect from the conference.
How do you help clients use Cheetah more effectively?
As a Wealth Management Consultant, I work closely with clients to help them understand and use Cheetah more effectively.
When a client first converts to Cheetah, they receive training on the entire system. That is a lot of information to take in at once, so it is natural that they may not remember every detail.
Part of my role is helping clients revisit the technology’s capabilities and connect them to the tasks they handle every day. Sometimes, a client has seen a feature before but has not started using it. When we demonstrate how it works and explain how to set it up, it can create an “aha” moment and introduce a better way to complete a familiar process.
What is your role at the Hunt?
I typically attend the Hunt with a few other members of the Wealth Management team. We often lead at least two operations-focused training sessions and work together to present the material and answer questions.
We try to make each session as practical as possible. The goal is for attendees to learn something they can take back to their organizations and apply right away. We want to give them tools that can make their workdays easier and help them accomplish their duties more effectively.
What makes the Hunt valuable for Cheetah clients?
One of the biggest benefits is learning more about how Cheetah can support their daily work.
In one session, we reviewed some of the platform’s background settings. We were surprised by how many attendees found that discussion valuable. The settings were already available within their systems, but it may have been a long time since they had reviewed them. Some attendees did not realize certain options were available or had forgotten how they could be used.
The Hunt gives clients time to step away from their usual responsibilities and take a closer look at the system. Even a refresher on familiar functionality can help someone identify a more efficient way to complete a task.
How does networking add to the conference experience?
Networking is another important part of the Hunt, especially in a field as specialized as trust and wealth management.
During breaks and between sessions, clients often seek out the Wealth Management Consultants to ask questions. Because we have worked with many different organizations, we may know another client who is using a particular feature or managing a similar process.
When appropriate, we can introduce those clients so they can share their experiences and learn from one another. Many Cheetah clients are willing to serve as resources for their peers. They exchange information, continue the conversation after the conference, and become part of one another’s professional networks.
That can be particularly valuable for professionals who work in smaller organizations or locations where they do not regularly interact with many other people in their field.
What have you learned from Hunt attendees?
For the past two years, I have participated in topic-centered roundtable breakout sessions. They work a little like speed networking. Attendees spend a short period at one table discussing a particular subject before moving to the next.
Although I am there to help answer questions, I also learn a great deal from those conversations. We hear directly from multiple clients about how they use a specific part of the platform.
Sometimes, a client has found a use that we had not considered. Learning how clients apply the technology in real-world situations gives us ideas we can share with other organizations facing similar challenges.
That exchange is part of what makes the Hunt so valuable. Cheetah experts share their knowledge with clients, but clients also learn from one another and teach us more about how the platform supports their work.
What can first-time attendees expect from the Hunt?
If you have not attended the Hunt before, you can expect to build valuable relationships with other professionals in your field.
You will also come away with new ideas for serving your clients, using Cheetah more effectively, and making your workday easier. The conference creates opportunities to revisit parts of the platform, ask questions directly, and hear how other organizations approach similar responsibilities.
For someone who has never attended, I would encourage them to take advantage of both sides of the experience. Attend the sessions and learn as much as possible, but also make time to speak with other attendees. Those conversations can be just as valuable as the formal training.
Continuing the conversation in Savannah
Jerry will return to the Hunt this year as trust and wealth management professionals from across the country gather in Savannah, Georgia. Through operations-focused sessions, informal conversations, and peer learning, he will continue helping attendees connect Cheetah’s capabilities to the work they do every day.
For Jerry, the conference is more than an opportunity to teach. It is also a chance to listen, learn how clients are using the platform, and help professionals throughout the industry build relationships that last beyond the event.
The Hunt takes place November 10 through 13 at The Westin Savannah Harbor Golf Resort & Spa. Visit the Hunt conference page to review the agenda and register.


