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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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Jessica Wilson


About Jessica

Meet Jessica, a seasoned professional with over 20 years of invaluable experience in the insurance industry. Her journey began in 2000, collaborating with a local doctor in the Tampa Bay area to navigate the complexities of insurance benefits. Eager to expand her expertise, she transitioned to a paralegal role in 2003, delving into the realm of first-party property claims, particularly focused on homeowners' insurance.


Under the guidance of a mentor, Jessica pursued her adjuster's license, unlocking new avenues in her career. Joining ROL Insurance Consulting in 2005, she steadily climbed the ladder to become a respected Claims Manager, honing her skills in managing intricate insurance claims. Her commitment and proficiency led her to Homeowners Choice Property and Casualty Insurance in 2012, where she supervised large-loss and complex homeowners' claims as a dedicated Claims Supervisor.


In 2014, Jessica embraced a new challenge at Bankers Insurance, assuming roles of increasing responsibility. Her journey culminated in her appointment as Director of Underwriting, where she excelled in guiding both Personal and Commercial Lines with finesse and strategic acumen.


Fueling her passion for continual growth, Jessica earned her Masters in Risk Management and Insurance from Florida State University in 2016, graduating with a stellar 4.0 GPA. Her thirst for innovation and leadership led her to spearhead the launch of The Hearth Insurance Group's homeowners' program in 2017, where she served as the General Manager of its Homeowners division.


Today, as a dedicated Brightway Agency Owner, Jessica is committed to leveraging her rich background and expertise to empower consumers with the knowledge to safeguard their assets effectively.


Beyond her professional endeavors, Jessica is deeply rooted in her community. A native of North Pinellas County, she resides in Palm Harbor with her family—her husband Rickey and their three wonderful children, Ethan, Landon, and Rhys. Their household is also graced by the presence of five adorable French Bulldogs—Titus, Remi, Reid, Theo, and Violet—and a beloved Staffordshire Terrier named "Big Mac."


In her leisure moments, Jessica finds solace in her love for music, skillfully playing the violin and cello. She also relishes time spent on the water, immersing herself in the beauty of nature. Moreover, Jessica actively contributes to her community as a dedicated Board Member of the Greater Palm Harbor YMCA and as the President Elect for the Rotary Club of Safety Harbor Noon, embodying her unwavering commitment to service and making a positive impact.

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 Erin

Erin Pooler is a Tampa, Florida native who has been married since 2005 and is the proud mother of two wonderful daughters. She relocated to Pinellas County six years ago and has fallen in love with the area, particularly enjoying its trails, beaches, and local restaurants, and visiting its breweries. Erin is also a devoted pet owner, with five French Bulldogs as part of her family.

Professionally, Erin initially held a 215 license and later obtained a 220 license. Erin supports her husband in running their screen business, demonstrating her strong commitment to both her family and professional endeavors. Erin's multifaceted roles as a wife, mother, entrepreneur, and licensed professional highlight her dedication and versatility within both her personal and professional life.

About Jackie

Jackie Tow is a dedicated insurance professional who embarked on her career journey in 2018, initially obtaining her 440 license while balancing the joys of motherhood as a stay-at-home mom to two beautiful children. In 2023, Jackie expanded her expertise by acquiring her 220 license and transitioning into a full-fledged agent. With an entrepreneurial spirit, she established her own agency, where she honed her skills and accumulated a wealth of knowledge in the insurance industry.


Driven by a passion for assisting others, Jackie made the decision in March 2024 to transition back into a collaborative team setting, where she continues her commitment to helping customers navigate the complexities of insurance. Her genuine desire to empower clients to understand their insurance needs and make informed decisions for themselves and their families is evident in every interaction.


Beyond her professional pursuits, Jackie finds solace and joy in various activities. She revels in the warmth of the sun, finds serenity by the beach, and enjoys the challenges and camaraderie of golf and yoga. Family time holds a special place in Jackie's heart, and she cherishes moments spent exploring theme parks with her beloved husband and children.


With her blend of expertise, empathy, and zest for life, Jackie Tow epitomizes a compassionate insurance professional dedicated to making a positive difference in the lives of those she serves.

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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