Based in RVi’s Orlando office, Principal Jack Caldwell, PLA, was recently promoted to Principal, marking the latest chapter in a career that began with an interest in golf course design. With more than 16 years of experience in landscape architecture, Jack’s work spans residential communities, institutional campuses, commercial development, streetscapes, and golf-focused projects.  

His work has taken him from master planning and site design through detailed design and construction, including projects such as the Florida Gulf Coast University Great Lawn, Esplanade communities across the Southeast, and Golden Ocala Golf & Equestrian Club.  

In this Employee Spotlight, Jack shares what continues to challenge and inspire him, the project that helped shape him as a landscape architect, how golf continues to influence his work, and what happens when a landscape architect decides to take on American Ninja Warrior. 

What inspired you to pursue a career in landscape architecture? 

My interest in landscape architecture began in high school, when I dreamed of becoming a golf course architect. As I explored that path, I learned that landscape architecture was the foundation for designing golf courses. That discovery introduced me to the broader possibilities of the profession and set me on the career path I’ve followed ever since.  

You were recently promoted to Principal. What does reaching this point in your career mean to you, and how do you see your role changing?  

If you had asked me three, five, or even 10 years ago if I would be capable of filling a Principal role at a firm like RVi, I probably would have doubted it. Reaching this point is a testament to the mentors I’ve had throughout my career and the opportunities I’ve had to grow. 

It’s incredibly rewarding to be part of a firm that creates a path for an ambitious, competitive person like me to achieve those career goals and recognize the hard work that goes into them. I’ve had mentors at RVi who have stuck with me through both failure and success. It hasn’t been a perfect path, and I’m certainly not perfect, but I think that’s part of the story. We learn from our failures and our successes, and we become who we are through that process. 

Looking ahead, I see my role shifting to focus more on strategically building teams, improving our systems and services, strengthening our client network, and taking greater ownership of the health of the business. I’m excited about the challenges ahead. 

You originally dreamed of becoming a golf course architect. How does that early passion for golf still influence the way you think about landscape architecture today?  

Golf was really the thing that connected me to the outdoors. It became a retreat from the stress of life as a young person—my escape and a place where I could connect with the outdoors in all kinds of environments. 

I grew up in Sebring, Florida, where we had lakes and golf courses everywhere, so golf became a big part of my life. I was a high school All-American and a scratch golfer. It was pretty consuming. 

As I got older, I realized I was ready for another chapter, but the passion for golf and design never completely went away. Today, I have the opportunity to design master-planned communities with golf courses, help plan the courses, and work alongside golf course architects through design and implementation. In that sense, it has really come full circle. 

It took 13 to 15 years before I started having the opportunity to play a key role in golf course planning and routing, and now I’m doing it pretty regularly. So, the dream didn’t completely go away. 

And for those wondering: Jack says his current golf handicap is about a 12. 

What has been your favorite or most challenging design project? 

The Great Lawn at Florida Gulf Coast University has been my favorite project so far. As an Associate Project Manager at the time, I learned more from this project than any other about the full design and implementation process—from stakeholder collaboration, client communication, and teamwork to contracts, scheduling, construction details, and execution.  

The project became a tangible expression of everything I was learning as I pursued my professional landscape architecture license, and it played a significant role in preparing me for and helping me pass the licensure exams.  

Most rewarding of all was seeing how the design influenced campus life—how people moved through the space, gathered there, and made it part of their daily experience. 

Is there another project that has particular significance to you? 

Esplanade at St. Marys in St. Marys, Georgia, stands out for a different reason. It was the first project where I really played a key role in the design. I was able to be involved up front in planning and design and then stay involved through execution alongside the golf course architect. 

Being able to help bring the course to life from start to finish made it especially meaningful. There are a lot of projects I could point to, but some become sentimental because they represent pivotal moments in your career. 

You compete in American Ninja Warrior competitions. How did this start?  

My daughter was five years old, and we loved watching the show together. She would just light up every time it came on, so I started looking for a gym where we could try it. 

We found one about a mile from our house. It had no air conditioning and there was a dumpster out front. It was basically a small industrial warehouse, but it gave us a place to learn and train. She absolutely fell in love with it, and I wanted to be alongside her on that journey, so I started training and competing with her. 

She’s now 13 and has been ranked in the top 10 in the world for the past four years. So, it’s become a really big part of our story. 

For me, it’s also a way to stay connected with her. Those moments become harder to find as kids get older, so I’m still trying to be the old guy who can keep up. I have a rip on my hand right now because of it, so it’s not always easy, but it’s worth it. 

I’ll be competing in Tampa soon, and my daughter is going to be my coach.