The perfect team — ready to guide you through your best options and solutions
Jennifer, Agency Manager
Jennifer, with over a decade of insurance and administrative experience, started at the front desk and quickly built her expertise. She enjoys the ever-changing nature of her work and helping clients make sense of insurance details—especially when it comes to complex policies.
When she’s not at work, you’ll find her dirt biking, boating, traveling, or spending time outdoors with her husband, kids, and her two French bulldogs, Zelly and Luna.
Joseph, Commercial Lines Agent
With nearly two decades in the insurance industry, Joseph began his career as an adjuster in 2005 before transitioning to the agency channel. He enjoys connecting with like-minded professionals and with a vast history and knowledge of commercial insurance, he enjoys helping clients navigate complex coverage challenges while building lasting relationships.
Outside of work, he loves riding his dirt bike, singing karaoke, and serving in his church community.
Phil, Personal Lines Agent
When Phil isn’t “binding and grinding,” you can usually find him jogging at the beach, kayaking, catching live concerts, or cheering on the Buffalo Bills. He loves being an insurance agent because it allows him to help people better understand their coverage and policies—explaining them in a clear, simple way so clients can make informed decisions.
Saving clients money along the way is an added bonus!
Deanna, Personal Lines Agent
Deanna is a proud Florida native who began her insurance career in 2018 and has since developed a deep expertise in coverage. She enjoys that every home and client brings something new, allowing her to build lasting and trusting relationships over the years.
Outside of work, she loves kayaking and hiking with her husband, kids and dogs, volunteering with her church and Wheelchairs 4 Kids, and exploring new recipes and creative projects—recently returning to her passion for stained glass art.
Kenzie, Personal Lines Agent
Kenzie has over five years of experience in the insurance industry, starting her career with little prior knowledge but quickly building expertise and confidence. She values connection and balance, spending free time with close friends and family—often enjoying a good hike on cloudy days.
As an independent agent, she enjoys the freedom to focus solely on each client’s needs, ensuring they receive the best coverage match rather than being tied to a single carrier.
Jessica, Personal Lines Agent
With seven years of experience in the insurance industry, Jessica is the newest addition to the Dockside Insurance Group team, bringing a dynamic expertise and a passion for helping clients navigate their coverage. She is dedicated to providing knowledgeable guidance in every client interaction.
Outside of work, Jessica enjoys running, traveling, and spending time outdoors.
Caroline, Service Agent
Caroline has worked in the insurance industry for over four years, beginning in customer service and continuing to expand her knowledge and expertise from her home base in Dunedin. She enjoys solving challenges and “playing detective” to help clients find the best solutions.
Outside of work, she loves exploring Florida’s natural beauty, swimming in rivers, and spending time with her family watching documentaries or playing board games.
Dale, Service Agent
Dale has worked in the insurance industry for over five years and enjoys the constant opportunities to learn and grow while helping clients navigate their coverage with confidence.
New to Pinellas County, he spends his free time exploring the area, traveling to new destinations with his wife, and spending weekends walking dogs and enjoying the outdoors.
Cameron, Marketing
Cameron worked as an inside adjuster for the National Flood Insurance Program from 2002-2014. This was followed by 10 years in the real estate industry giving her perspective of both insurance claims and issues her clients faced with everyday homeownership and real estate transactions. While it was difficult to see the destruction of communities, she found value in being a part of the recovery, guiding home and business owners through the process of rebuilding, and watching numerous communities come together with a singular focus.
She is a lifelong singer, classically trained with experience in operatic singing, and currently playing local venues with a 4–12-piece folk/rock band as a member for over 15 years.
She enjoys being on her boat for days at a time as well as fishing and paddleboarding with her husband and friends, and loves working with animals. She is a native of Dunedin, Florida but also enjoys spending time in the mountains of Western Carolina and can often be caught talking to random woodland animals that may or may not respond.
Cameron manages agency marketing as well as client experience, and is involved in day-to-day operations.
James, Agency Principal
James began his insurance career in 1997, starting as an auto claims adjuster with Liberty Mutual before transitioning to a field adjuster role with the National Flood Insurance Program (NFIP). Over the next 15 years, he was deployed to 36 states, assisting communities in some of the most disaster-stricken areas across the country. Through those experiences, James developed a deep appreciation for the challenges families and businesses face after catastrophic floods—and a passion for helping them recover.
Having worked with thousands of homeowners, business owners, and agents during some of life’s most difficult moments, James brings a level of flood insurance expertise that is virtually unmatched nationwide. He holds a current Flood Control Number (FCN) issued by FEMA for all major categories—Residential, Large Commercial, Manufactured Home, and Condominium (RCBAP)—as well as active licenses in life, annuity, health, property, and casualty insurance, and an all-lines adjuster license. In addition, he has earned the Accredited Claims Adjuster (ACA) designation through the University of Central Florida School of Insurance.
A proud Florida native, James enjoys spending his free time outdoors—whether on the water, in the air, or exploring nature. An avid fisherman, he loves inshore and fly fishing from the Florida coast to the mountains of North Carolina. He also holds a U.S. Coast Guard 100-Ton Captain’s License and an FAA Private Pilot’s License. Above all, James values his family, lifelong friendships, and the meaningful connections built through helping others protect what matters most.
James is passionate about using his decades of experience to help individuals and businesses safeguard their futures and everything they’ve worked so hard to achieve.
