Meet Your Wilson Agency Brightway Insurance Team

Jessica brings nearly 20 years’ experience in the insurance industry to Brightway. She began her career in the industry in 2000 while working with a local doctor in the Tampa Bay area handling insurance benefits. 

In 2003, she joined an attorney’s office in the Tampa Bay area as a paralegal handling first party property claims, primarily homeowners’ claims.  While working in that role, she was mentored by a colleague in the insurance industry which encouraged her to get her adjuster’s license. 

She joined ROL Insurance Consulting as a Claims Adjuster in 2005 and worked her way up the ranks to Claims Manager during her tenure there.

In 2012, she joined Homeowners Choice Property and Casualty Insurance as a Claims Supervisor overseeing large loss/complex Homeowners’ claims. In 2014, she went on to work for Bankers Insurance and served as a Director of Claims of both Personal and Commercial Lines, eventually rising to the role of Director of Underwriting.

In 2017, she helped launch The Hearth Insurance Group's homeowners' program as the General Manager of its Homeowners division.

In 2016, Jessica earned a Masters in Risk Management and Insurance from Florida State University, graduating with a 4.0 GPA.

As a Brightway Agency Owner, she looks forward to using her background and expertise to educate consumers on protecting their assets. 

Jessica, who grew up in North Pinellas County, lives in Palm Harbor with her family which includes her husband and agency partner Rickey and their three children -  Ethan, Landon and Rhys. They also are mom and dad to two sweet French Bulldogs - Kate and Titus.

She spends her free time playing violin, serving on the Worship & Arts team at Palm Harbor United Methodist Church, boating, and paddle boarding. 

Jessica serves with both Boy Scouts Troop 26 and Girl Scouts Troop 927 which her children are very active in. She also serves on the PTA for both Lake St. George Elementary and Palm Harbor Middle School.  

She is fluent in American Sign Language. 

Before becoming a Brightway Agency Owner, Rickey spent 20 years working in the real estate and construction industry.

He earned both his bachelor's degree and MBA from Florida State University.

In the State of Florida, he is a Certified General Contractor, Certified Home Inspector, Licensed Realtor and a Licensed Insurance Adjuster. 

As a Brightway Agency Owner, Rickey enjoys connecting with people, learning about their everyday life and business and how he can help make sure they are protected.

Rickey lives in Palm Harbor with his family which includes his wife and agency partner Jessica, their three children and two French bulldogs. 

Aside from spending time with his family, Rickey is an avid fisherman. 

He serves on the Advisory Board for the Pinellas County Economic Development Council, The School Advisory Board for St James Cathedral School in Orlando, FL and on the Advisory Board for the Greater Palm Harbor YMCA.