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Meet Your Wilson Agency Brightway Insurance Team

The key to exceptional insurance coverage starts with an agent who truly understands your needs. Our Wilson Agency team lives right here in the community. We know the unique risks, assets, and lifestyles of Safety Harbor and the surrounding Tampa Bay area communities residents.
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500 Main Street
Suite L
Safety Harbor, FL 34695

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727-316-5004

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Jessica Wilson
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About Jessica

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 four sweet French Bulldogs - Titus, Remi, Reid and Valentina.

She spends her free time playing violin and cello, serving on the Board of Directors for the Greater Palm Harbor YMCA, and serving as President Elect with the Rotary Club of Safety Harbor Noon and boating.

About Rickey

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.

About Nikole

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.

About Kathy

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.

About Lisa

Lisa is a local expert. Born and raised in the Tampa Bay area, she is definitely a true native. She graduated from the University of South Florida with a Bachelor’s Degree and is working on her Master’s degree.

Having worked with a national insurance company for three years, she made the decision to stay home and raise her two beautiful children, now ages 17 and 15. When it was time to come back, she started with the Brightway family and fell back in the love with insurance.

She is an avid reader and loves to do anything with crafting including scrapbooking and crocheting. 

About Jake

Jake is a St. Petersburg native who worked in Mortgage and Finance prior to joining Brightway, The Wilson Agency.

In his free time, he loves hanging out with his dogs and supporting his favorite sports team: the Lightning, Seminoles and Inter Milan.

He believes in creating customers for life and believes there is no higher praise than a referral!

About Sarah

Sarah is new to both Brightway and the insurance industry but is quickly learning the ropes from the experts at Brightway, The Wilson Agency. She began her insurance career in 2022 and obtained her 4-40 license in 2023, after working in mortgages since 2010.

Sarah grew up in Northeast Ohio, where she graduated from Bohecker College with a bachelor's degree in business.

Sarah moved to Florida in 2008 to enjoy warm weather year-round. She loves going to the beach, boating, bike riding or visiting the park with her Doberman named Atlas.

Sarah's passion is helping people. In her free time, she volunteers with The Children's Dream Fund and The St. Pete Fools Club.

Visit us to learn more about Safety Harbor and the surrounding Tampa Bay area communities Insurance

We're eager to help you find the right insurance online or in-person. Visit our office to meet your new insurance team.

Our Office

500 Main Street
Suite L
Safety Harbor, FL 34695

Office Hours

Monday-Friday: 9 a.m. to 5 p.m.
Saturday-Sunday: Closed

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