Jessica Wilson

Meet Jessica Wilson — a seasoned insurance professional with over 25 years of expertise and a passion for helping others protect what matters most. Jessica’s career began in 2000 in Tampa Bay, assisting a local physician with insurance benefits. Driven to expand her knowledge, she transitioned to a paralegal role in 2003, focusing on first-party property claims, especially homeowners’ insurance.

Mentored by industry leaders, Jessica earned her adjuster’s license and joined ROL Insurance Consulting in 2005, rising to Claims Manager. Her journey continued with leadership roles at Homeowners Choice Property & Casualty Insurance and Bankers Insurance, where she ultimately served as Director of Underwriting for Personal and Commercial Lines. In 2016, Jessica graduated with a Master’s in Risk Management & Insurance from Florida State University with a 4.0 GPA. The following year, she led the launch of The Hearth Insurance Group’s homeowners’ program as General Manager.

Today, Jessica proudly owns and operates Brightway, The Wilson Agency, serving families and businesses across Tampa Bay and Florida’s Nature Coast. She is currently expanding to a second location in Homosassa, bringing her wealth of knowledge and heart-driven service to even more clients.
Jessica’s roots run deep in North Pinellas County, where she lived for over 30 years before moving to the Nature Coast with her husband, Rickey, and their three children — Ethan, Landon, and Rhys. Their bustling mini-farm is home to a lovable crew of five French Bulldogs (including Yoshi, their courageous wheelchair warrior), a Staffordshire Terrier, a German Shorthaired Pointer, Highland Mini Cows, goats, chickens, turkeys, and sheep.

In addition to running her agency and her farm, Jessica is a passionate community leader. She served as President of the Rotary Club of Safety Harbor Noon (2024-2025) and is the current President of the Rotary in the Harbor Foundation, spearheading local service projects and fundraising efforts.
In her downtime, Jessica embraces her love of music, playing violin and cello, and enjoys exploring the waterways and natural beauty of Florida’s Gulf Coast. Whether she’s building her business, serving her community, or wrangling her joyful animal crew, Jessica leads with energy, heart, and purpose — and she’s excited for what’s ahead!