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Welcome to Brightway, The Wilson Agency

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Shining Sun A more personal way to shop insurance.


When it comes to buying insurance, Brightway, The Wilson Agency, is your source for more choices and better service. Whether you’re looking for a competitive rate for Homeowners insurance or need help determining the right amount of auto coverage, you’ll receive personal attention from industry experts committed to your satisfaction. If we can answer any questions about Home, Auto, Flood or other types of insurance, give us a call or send us an email. 

Shining Sun Providing our customers with high levels of service.

Jessica Wilson
Jessica Wilson Agency Owner

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. 

  • Jessica Wilson
    Jessica Wilson Agency Owner

    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. 

    Jessica Wilson Agency Owner
    Jessica Wilson
    Jessica Wilson Agency Owner

    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. 

  • Rickey Wilson
    Rickey Wilson Agency Owner

    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. 

     

     

    Rickey Wilson Agency Owner
    Rickey Wilson
    Rickey Wilson Agency Owner

    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. 

     

     

Yellow Sun Shine Our reputation says it all.


  • We recently had the absolute pleasure of working with Jessica Wilson for our insurance needs. She was always prompt to follow up and she has an extensive knowledge of what is needed to accurately write the most comprehensive and cost sensitive policy. We appreciated her professionalism and how she valued us as a customer. I will recommend Jessica to any of my friends and colleagues who are in the market for any type of insurance.

    Lynne B.

  • After not shopping for auto insurance for the better part of a decade, I found myself undercovered and overpaying. My Brightway Agent was able to find me a policy that tripled my coverage while lowering my premium! My wife and I are thrilled with what Brightway, The Wilson Agency was able to do for our family.

    Andrew L.

  • My Brightway Agent found a policy that doubled my auto coverage. And at a cheaper rate than I had been paying for two years. Thank you Wilson Agency Team!

    Kevin P.

  • I highly recommend the Wilson Agency. They recently provided an individualized evaluation of the coverage I would need for my new condo. The choice of carriers was great and the prices were reasonable.

    Andrea O.

  • Your first time purchasing a home can be quite overwhelming on many levels. The Wilson Agency made searching for the perfect insurance policy a breeze for me! Jessica took that weight off my shoulders so I could deal with other things along the way and was extremely helpful and informative. I appreciate all your hard work and highly recommend anyone needing new insurance to visit the Wilson Agency!

    Melissa C.

  • Jessica was such a help! I asked her to help out with getting me a quote for my salon. She was so professional and knows her stuff. She also got my auto under the same umbrella so I'm saving money. Best part is Jessica reached out and keeps me updated on when things need paid and ect. Best experience ever! She made what is usually a painful task, Jessica made easy, effortless and knowledgeable. As soon as I get my roof finished I'll be going to her for homeowners as well.

    Nicole L.

Yellow Sun Shine More choice. More convenience. More confidence.


Yellow Sun Shine Visit us today.


Give us a Call
727-316-5004
Our Office

670 2nd Street North Unit D
Safety Harbor, FL 34695

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Hours of Operation

Monday: 9 a.m. to 5 p.m.
Tuesday: 9 a.m. to 5 p.m.
Wednesday: 9 a.m. to 5 p.m.
Thursday: 9 a.m. to 5 p.m.
Friday: 9 a.m. to 5 p.m.
Saturday: Closed
Sunday: Closed

Let us find the right insurance for you.


Reach out and we’ll get back to you with a custom policy that fits your unique situation.

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