Gail Fitzsimmons

I’ve been working as an employee benefits account manager with ARCW Leavitt since May 2022, and it’s been an incredibly rewarding chapter in my career. Before entering the insurance world, I proudly served over 20 years in the United States Air Force, retiring as a Master Sergeant (E-7). My time in the military naturally transitioned me into human resources, where I earned my degrees and spent several years gaining experience across multiple industries—including senior living, audio visual, and federal contracting—as an HR manager and benefits manager.

While working remotely during the COVID years, I found myself ready for a new challenge. That’s when I decided to get my Florida Health, Life & Annuity 215 License and shift into the broker side of employee benefits. Now, as an account manager, I get to combine my HR background with client service, helping employers and employees navigate the often-complicated world of healthcare and benefits.

What I enjoy most about my job is working with such a supportive team and being able to help people, especially when I can solve a problem or make something less confusing for a client or their employee. That kind of impact is what drives me.

Outside of work, I’m loving life in my new hometown of St. Augustine, Florida. I enjoy getting outdoors, exploring the area’s rich history and culture, and staying active. You’ll often find me walking, biking, kayaking, paddle boarding (I’m still learning!), or just spending time with my family soaking up the Florida sunshine.