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Providing local expertise and the power of choice is the Brightway difference.

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.

Jessica graduated from Florida State University with a Masters in Risk Management and Insurance with a 4.0 GPA in 2016. She helped launch The Hearth Insurance Group's homeowners' program as the General Manager of its Homeowners division in 2017.

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 Rickey and their three children, Ethan, Landon and Rhys. They also are mom and dad to three sweet French Bulldogs, Titus, Remi and Reid.

She spends her free time playing violin, serving on the Board of Directors for the Greater Palm Harbor YMCA, serving with the Dunedin North Rotary and boating.

  • 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.

    Jessica graduated from Florida State University with a Masters in Risk Management and Insurance with a 4.0 GPA in 2016. She helped launch The Hearth Insurance Group's homeowners' program as the General Manager of its Homeowners division in 2017.

    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 Rickey and their three children, Ethan, Landon and Rhys. They also are mom and dad to three sweet French Bulldogs, Titus, Remi and Reid.

    She spends her free time playing violin, serving on the Board of Directors for the Greater Palm Harbor YMCA, serving with the Dunedin North Rotary and boating.

    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.

    Jessica graduated from Florida State University with a Masters in Risk Management and Insurance with a 4.0 GPA in 2016. She helped launch The Hearth Insurance Group's homeowners' program as the General Manager of its Homeowners division in 2017.

    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 Rickey and their three children, Ethan, Landon and Rhys. They also are mom and dad to three sweet French Bulldogs, Titus, Remi and Reid.

    She spends her free time playing violin, serving on the Board of Directors for the Greater Palm Harbor YMCA, serving with the Dunedin North Rotary and boating.

  • 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.

  • Nikole Wellman
    Nikole Wellman Licensed Agent

    Nikole is an insurance expert with more than 12 years of experience. Growing up in Michigan she knows what the cold is really like. She moved to Virginia and earned a bachelor’s degree from the University of Mary Washington. She started her insurance career in 2010 in Virginia.

    In 2013, she moved her family to the beautiful Sunshine State. She is an expert personal lines insurance advisor working with individuals to identify and evaluate their personal risks and offer the best customized solutions.

    When Nikole is not working, you can find her spending time with her three children and two granddaughters. She loves biking on the Pinellas Trail or going out on the boat in the Gulf. Giving back to the community is extremely important to Nikole. She is active with community service events and projects and is the past President for the Rotary Club of Dunedin Waterside.

    Nikole Wellman Licensed Agent
    Nikole Wellman
    Nikole Wellman Licensed Agent

    Nikole is an insurance expert with more than 12 years of experience. Growing up in Michigan she knows what the cold is really like. She moved to Virginia and earned a bachelor’s degree from the University of Mary Washington. She started her insurance career in 2010 in Virginia.

    In 2013, she moved her family to the beautiful Sunshine State. She is an expert personal lines insurance advisor working with individuals to identify and evaluate their personal risks and offer the best customized solutions.

    When Nikole is not working, you can find her spending time with her three children and two granddaughters. She loves biking on the Pinellas Trail or going out on the boat in the Gulf. Giving back to the community is extremely important to Nikole. She is active with community service events and projects and is the past President for the Rotary Club of Dunedin Waterside.

  • Jessica Kaylor
    Jessica Kaylor Licensed Agent

    Jessica Kaylor began her insurance career in 2013 and is a Florida licensed Property & Casualty agent. She holds a BAS in Supervision and Management in Organization Administration from Pasco Hernando State College and has a true passion for the insurance industry. She enjoys providing her clients the peace of mind that comes with customized protection. Ultimately, she takes pride in knowing that her efforts have resulted in educating her clients on the best options of personalized insurance coverage. 

    Jessica was born and raised in the Tampa Bay area and loves living, working and playing in the sunshine state. When she isn’t providing excellent service to her clients, you can find her hanging in her hammock with a book in her hand, on a bike riding around downtown St. Pete or on a boat with her friends. She loves to travel the world in her free time, discover new places and most importantly learn about different cultures.

    Jessica Kaylor Licensed Agent
    Jessica Kaylor
    Jessica Kaylor Licensed Agent

    Jessica Kaylor began her insurance career in 2013 and is a Florida licensed Property & Casualty agent. She holds a BAS in Supervision and Management in Organization Administration from Pasco Hernando State College and has a true passion for the insurance industry. She enjoys providing her clients the peace of mind that comes with customized protection. Ultimately, she takes pride in knowing that her efforts have resulted in educating her clients on the best options of personalized insurance coverage. 

    Jessica was born and raised in the Tampa Bay area and loves living, working and playing in the sunshine state. When she isn’t providing excellent service to her clients, you can find her hanging in her hammock with a book in her hand, on a bike riding around downtown St. Pete or on a boat with her friends. She loves to travel the world in her free time, discover new places and most importantly learn about different cultures.

  • Kathy Lane
    Kathy Lane Licensed Agent

    Kathy is a local expert, having been born and raised in the Tampa Bay Area. She graduated from Palm Harbor University High School and married her high school sweetheart.

    Her husband was in the Navy and they lived in Texas for two years before returning home to Florida. She worked in the veterinary field for 10 years and during that time had two beautiful children.

    After the birth of their baby girl, it was time for a career change. Brightway was able to offer a position that allowed her to care for her family while still engaging her skills and expanding her knowledge of the insurance industry. Since her hire, she has obtained her 4-40 license.

    As an animal lover, she also cares for two dogs and two cats.

    Kathy Lane Licensed Agent
    Kathy Lane
    Kathy Lane Licensed Agent

    Kathy is a local expert, having been born and raised in the Tampa Bay Area. She graduated from Palm Harbor University High School and married her high school sweetheart.

    Her husband was in the Navy and they lived in Texas for two years before returning home to Florida. She worked in the veterinary field for 10 years and during that time had two beautiful children.

    After the birth of their baby girl, it was time for a career change. Brightway was able to offer a position that allowed her to care for her family while still engaging her skills and expanding her knowledge of the insurance industry. Since her hire, she has obtained her 4-40 license.

    As an animal lover, she also cares for two dogs and two cats.

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.


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Give us a Call

727-316-5004

Our Office

500 Main Street Suite L
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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