We Are a Health Insurance Agency
After 11 years of working in the financial industry, Steven Riddle decided to pursue more value in his services. In 2008, he became licensed as an insurance agent, and in 2013, he joined United Healthcare as an independent career agent. At that point in his career, Steven spent most of his time in the Medicare Field, helping hundreds of beneficiaries each year. Later, his wife Denisse Riddle and daughter Jahnieli Cruse became licensed agents, and together they founded “The Riddle Family Insurance.”
The Riddle Family Insurance is a family-owned agency in Plant City, Florida. Our value is in being an independent agency that represents the best insurance carriers in the area. We are not exclusive with any company, therefore; we can offer an unbiased opinion. Our thorough needs assessment helps us understand the priorities of our customers enabling them to choose the best plan for their needs.
Our Mission
Riddle Family Insurance is a loyal family-oriented Medicare and Health Insurance Agency in Plant City, FL. The office is located in the skirts of downtown Plant City and is available to help you with all Health, Medicare, and Life Insurance.
Founded in 2008, we are a family-owned and operated business focused on the client’s needs. Having a large variety of plans available, plans and rates can be shopped, and clients can be given the best coverage.
As a local insurance agency, our mission is to provide our community with the best standards of service. We are committed to treating our clients like family, keeping close relationships by being available for your insurance needs.
Denisse Riddle
Licensed Insurance Agent
Marketing Director
Denisse Riddle is a woman of faith; she attended Victory Church in Lakeland and prayed that she would meet her future husband there. In 2016, the love of her life sat right behind her just as she asked the Lord for the right husband. He decided she was the one and married her in 2017, forming a beautiful, blended family with 5 kids. About a year later, Denisse noticed how much Steve enjoyed his job as a Health Insurance Agent with United Healthcare and the opportunities this career could bring to help people in the community and church. Together, they decided it was time to leave her job and form “The Riddle Family Insurance,” now known as Riddle Insurance Solutions.
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Short Biography
Denisse began her career as an insurance agent back in 2000 as an independent agent with Aflac in Puerto Rico. However, she left her career for a time in her life to dedicate herself to her family. Later, some unexpected events in life brought her to start from nothing again as a single mom with 4 girls, moving to the great state of Florida. In 2014, she landed a job as an assistant manager for Hobby Lobby in Lakeland, Florida, and four years later, she re-licensed for the state of Florida. Since then, she has been working as an independent insurance agent, starting with United Healthcare and as a co-owner of “Riddle Insurance Solutions,” where they offer multiple services specializing in Individual Health and Medicare, Small Businesses Insurance, Schools, Non-profits, and Church Insurance.
In addition to being a business owner, Denisse is active as a board member of Aspire and an ambassador with The Great Chamber of Commerce in Plant City. If you are in love with Plant City like she is, you will probably see her working and volunteering in many events or playing tennis at the Plant City Tennis Courts and Lakeland Beerman Courts.
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Areas of Expertise
When Denisse started with United Healthcare, she mainly helped Hispanic seniors. Even though she is fluent in both languages, the demand for Hispanics moving to the area kept her busy. Since then, she has worked with Hispanic low-income seniors and their families. As she worked with all Medicaid applications, she discovered that every case was different, and she thoroughly learned the different ways to keep all the family covered including those that are self-employed or own small businesses.
Jahnieli Cruse
Licensed Insurance Agent
You will never get tired of talking with Jahnieli! She enjoys learning thru other people’s stories and she has the gift of paying close attention to what others say. This fine young lady loves to dance, cook, and occasionally take a full day in front of the beach and just do nothing but relax.
Jahnieli Cruse attends Victory Church in Lakeland and serves in many areas, like kid’s ministry, Spanish translation, Student Church, and College Students. She manages herself well in covering many areas of her life including her husband, family, and giving great quality service to all her members.
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Short Biography
Jahnieli Cruse became a Licensed Insurance Agent in 2018 and has been working with The Riddle Family Insurance as an independent agent since then. She graduated from Southeastern University in 2022 with a bachelor’s degree in Ministerial Leadership. Currently, she is the creator of “Baila,” which takes place at different community centers in Plant City and is a free service to everyone.
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Areas of Expertise
One of Jahnieli's first experiences as an agent was helping one of her clients with her diabetes prescriptions. After seeing how she helped to save this client about $300 per month, Jahnieli has had a passion for people with chronic diseases that are spending too much on their medicines.
Steven Riddle
Licensed Insurance Agent
Agent Manager
Steven Riddle is a very fun person to be around, especially when you bring up some of his favorite conversational topics, like tennis, business, and God. You will probably find Steven eating a donut and a coffee every Sunday between services at Victory Church Lakeland. He is a family man and enjoys being around the family; he brought his wife and daughter into sharing the same career and shares his office with his mom “Darla.” Steve is a Rotarian and always eager to be involved in the Plant City Community, and looks forward to serving the community for many years to come.
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Short Biography
At the age of 11, Steven moved to Plant City with his parents and sister. His father, Walter Riddle, relocated their family business from Texas, establishing a permanent location on Dr. Martin Luther King Jr. Blvd in Plant City, where Steven has maintained his office since 1998. Steven enjoyed learning and working with his dad across various entrepreneurial ventures, and in 2013, he launched his Medicare Insurance career.
Steven began his career as an Independent Career Agent with United Healthcare, starting at the WellMed office in Plant City and the Strawberry Cruise in Downtown Plant City. He diligently set up tables at these locations, fostering strong relationships with WellMed and the Chamber of Commerce. Through his commitment, Steven has assisted the community with their Medicare and Medicaid needs, serving thousands of Plant City residents. He continues to build relationships with doctors and possesses extensive knowledge of the medical care industry.
In 2006, Steven earned his Master’s in Business Administration from Southeastern University in Lakeland and has always sought opportunities to work with small businesses. In addition to his Health and Life License and Real Estate Broker’s License, he obtained his Property and Casualty License to better serve small businesses, including churches, schools, and non-profits, with their insurance needs.
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Areas of Expertise
With years of experience, Steven excels in assisting clients as they turn 65 or retire. He knows exactly where to start and guides them from beginning to end, whether they choose to stay with their current plan or start their Medicare Part B. Many employees from Mosaic, Hillsborough, and Polk County Schools, Publix, and other major employers have chosen him for his reliable expertise.
Additionally, Steven’s education and extensive experience working with small businesses and real estate have given him a broad knowledge of Small Business Insurance, including Workers’ Compensation and Commercial Property Insurance.
Cynthia Kropp
Licensed Insurance Agent
Business Advisor
Cynthia is known for her sweet and supportive nature. Always willing to lend a hand, Cynthia thrives on connecting with people and learning the unique culture of every business she visits. With her warm demeanor and genuine curiosity, she quickly builds rapport and gains a deep understanding of each client's needs. Cynthia's confidence and ability to engage with others make her an invaluable asset to our team, ensuring that our clients feel understood and well cared for from the very first interaction.
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Short Biography
Our family has been living in Plant City since 2014. My husband, Brian, and I have five children, whom I homeschooled for over 20 years. I have served on the Plant City Area Soccer Club’s Board of Directors for over 6 years. I enjoy watching soccer, especially since all my children love it and have played at the college level. I have served as an Elections Clerk in 2020 and 2024.
I worked for a small employer for over 10 years and have several family members who have started their own businesses. I am passionate about helping small business owners. I have been a Benefits Counselor for over 3 years. As a Benefits Advisor with Riddle Insurance Solutions, my knowledge and skills in the area of employee benefits give me a great opportunity to walk alongside owners and assist them in helping bring value to their employees and driving the business to the next level.
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Areas of Expertise
Cynthia Kropp brings a wealth of expertise to Riddle Insurance Solutions, specializing in a broad range of employee benefits and insurance solutions. With deep knowledge in Individual Coverage Health Reimbursement Arrangements (ICHRA), Qualified Small Employer Health Reimbursement Arrangements (QSEHRA), and both level-funded and fully insured group insurance plans, Cynthia is equipped to tailor benefits packages that meet the unique needs of any business.
Her proficiency extends to navigating the complexities of employee compliance, ensuring that both small and large businesses adhere to regulatory requirements with ease. Whether it’s guiding clients through compliance forms or helping them implement comprehensive benefits strategies, Cynthia's expertise ensures that every business she works with is well-protected and fully compliant.
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