Meet Your Wilson Agency Brightway Insurance Team

With more than 25 years of experience in the insurance industry, Jessica Wilson has built her career around one simple mission: helping people understand risk, protect what matters most, and navigate insurance with confidence.

Jessica’s insurance journey began in 2000 in the Tampa Bay area, where she worked alongside a local physician navigating insurance benefits. In 2003, she transitioned into the legal field as a paralegal specializing in first-party property claims, giving her an early and invaluable perspective into homeowners insurance and the claims process.

Encouraged by a mentor to pursue her adjuster’s license, Jessica joined ROL Insurance Consulting in 2005 and ultimately advanced to Claims Manager. In 2012, she joined Homeowners Choice Property & Casualty Insurance, supervising large-loss and complex homeowners claims.

Her career took another major step forward in 2014 when she joined Bankers Insurance, where she held positions of increasing responsibility before becoming Director of Underwriting, overseeing both Personal and Commercial Lines.

Committed to becoming a true student of the industry, Jessica earned her Master’s degree in Risk Management and Insurance from Florida State University in 2016, graduating with a 4.0 GPA. In 2017, she helped launch The Hearth Insurance Group’s homeowners program and served as General Manager of its Homeowners division.

Today, Jessica is the proud owner of Brightway, The Wilson Agency, a multi-unit independent insurance agency serving clients throughout Florida. After years of building a successful agency in Safety Harbor, Jessica and her team expanded to Florida’s Nature Coast, bringing the agency’s commitment to education, choice, and exceptional client service to Citrus County and the surrounding communities.

Jessica believes insurance should never be about simply finding the cheapest policy. With experience spanning claims, underwriting, carrier operations, risk management, and agency ownership, she brings a unique 360-degree perspective to helping individuals, families, and businesses make informed decisions about protecting their assets.

Beyond Insurance

After more than 30 years in North Pinellas County, Jessica and her husband, Rickey, traded suburbia for the wide-open spaces of Florida’s Nature Coast, where they live with their three children, Ethan, Landon, and Rhys—and a family of animals that seems determined to keep growing.

Their home has become a lively rescue-filled farm featuring French Bulldog rescues, including Yoshi, their fearless wheelchair warrior, along with Highland mini cows, goats, chickens, a donkey, horse, alpacas, pigs, and other four-legged personalities who have found their way into the Wilson family.

Jessica’s love for animals also inspired another important chapter: Rolling Into Hope Rescue Ranch, a nonprofit dedicated to raising funds and awareness for special-needs and at-risk animals and supporting the rescues, veterinary professionals, and rehabilitation organizations working to give them a second chance.

Community service is equally important to Jessica. She is actively involved with Rotary, Leadership Citrus, the YMCA, and Rolling Into Hope Rescue Ranch, and believes that being successful in business also means being willing to invest your time, resources, and energy back into the community you call home.

When she isn’t running two insurance agencies, working on a community project, fundraising, or tending to the farm, Jessica enjoys being on the water and embracing her lifelong love of music through the violin and cello.

Her worlds may seem wonderfully varied—insurance, entrepreneurship, community service, rescue animals, farming, family, and music—but they are connected by the same thing: a genuine passion for building something meaningful and leaving people, animals, and communities better than she found them.

And if there’s one thing Jessica has learned along the way, it’s that there is always room for one more big idea...and apparently, one more animal.

Before becoming a Brightway Agency Owner, Rickey spent over 25 years immersed in the real estate and construction industries, working across 25 states. With both a bachelor’s degree and an MBA from Florida State University, Rickey is a firm believer in lifelong learning and continuing education.

In Florida, he holds multiple certifications and licenses, including Certified General Contractor, Certified Home Inspector, Licensed Realtor, and Licensed Insurance Adjuster.

As a Brightway Agency Owner, Rickey thrives on building meaningful connections, learning about his clients’ lives and businesses, and helping them ensure they have the right protection in place.

Rickey calls Crystal River home, where he lives with his wife and business partner, Jessica, their three children, and a variety of animals. When he’s not spending quality time with his family, Rickey is an avid outdoorsman who enjoys every opportunity to be on the water.

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.

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. 

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.

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.