Why I Created
Creative Comp Solutions

Meet Jena Caldwell — Founder & CEO of Creative Comp Solutions

Jena’s roots in the claims industry run deep. It started with her grandfather, passed through her mother — who wrapped up a 40-year career as a Chief Claims Officer — and eventually led Jena to build her own path in the field she grew up around.

While earning her Bachelor’s in Advertising & Public Relations (Cum Laude) with a Minor in Marketing from The Burnett Honors College at the University of Central Florida, Jena held various roles at an insurance company, giving her a strong foundation early on. After graduating, she launched her career in Ancillary Services as an Account Manager for a national provider — and never looked back.

Over the past two decades, Jena has worked across Ancillary Services, Defense Law, Investigations, and Case Management, holding leadership roles including National Sales Director and Vice President of Sales & Marketing. Through it all, one thing remained clear: Clients already have enough on their plate — they deserve a partner who steps in, adds value, and makes their job easier.

That’s why she created Creative Comp Solutions — a company built on urgency, trust, and follow-through. Jena doesn’t believe in making her clients chase answers or settle for less. She shows up, solves problems, and helps claim professionals stay in control by containing costs, controlling overutilization, and keeping everyone updated — every step of the way.

When you grow up in claims, you don’t just understand the pressure — you build something that relieves it.

Jena now runs Creative Comp Solutions alongside her husband, James, who serves as CFO. They live in Florida with their three daughters. Outside of work, you’ll find her in the kitchen cooking Italian classics or dressing her girls to the nines — usually both at once.

With almost two decades of experience in financial planning for businesses and families, James brings extensive financial knowledge for long-term strategic growth. James first attended Western Kentucky University as a Division 1 football player before transferring to The University of Central Florida where he graduated with a Bachelor’s in Finance. James has spent most of his career helping business and families protect and grow their wealth. He is a Registered Investment Advisor, holding his Series 7, Series 66, and FL 215. It’s his wealth of knowledge and leadership that brings the best of class guidance to Creative Comp Solutions and its financial well-being. James is married to Creative Comp Solutions’ CEO Jena, and they live in Florida with their three daughters. Outside of work, James loves boating, fishing, and entertaining his daughters. His love for the outdoors fails in comparison to his love of enjoying Jena’s classic Italian meals.