Self-Insured Plans

Jessica Sista is a licensed Life and Health Insurance Agent with a well-rounded background in finance, communications, and entrepreneurship. She began her career in the finance and mortgage industry before moving into pricing and communications for a national retail company, where she strengthened her skills in strategic planning and client engagement.

In 2017, she co-founded an online retail business, gaining hands-on experience in operations, branding, and social media. This entrepreneurial journey sparked her interest in employee benefits and deepened her passion for helping clients navigate coverage with clarity and confidence.

Jessica brings a solution-focused mindset and a strong commitment to client service, drawing from her diverse experience to support employers and their teams.

Sheri Bell is a licensed Life and Health Insurance Agent with over 25 years of experience in employee benefits. She holds a Business degree from Oakland City University and is known for her ability to guide clients through the complexities of benefits with clarity and care. Sheri’s dedication, proactive approach, and people-first mindset make her a trusted partner in navigating employee benefits. Outside of work, she enjoys spending time with her husband of 41 years, Greg, and their five sons and eight grandchildren.

Shanna Driscoll has a bachelor’s in business administration from Arizona State University and has 5+ years as a licensed life and health agent. As a Strategic Solutions Provider she determines how to best utilize the talents of our team to benefit your company and associates. In addition to her organizational sales role, she specializes in employee benefit consultation, specifically large group account optimization and technology integration, as well as comprehensive all-in-one client service.

Isaac Ebury is a US Army Veteran and has a bachelor’s degree in business management from Stetson University. He has years of experience in operations management and small-team leadership from his time in the US Army and has served in multiple leadership roles in other organizations. As a strategic solutions provider, Isaac specializes in connecting groups of all sizes to The Enterprise Team’s range of innovative and strategic employee benefits management solutions.

Lynne Mahn is a licensed Life and Health Insurance Agent with over 15 years of experience in the employee benefits industry. She specializes in large-group account management and is known for her integrity, client advocacy, and commitment to delivering best-in-class service. Lynne builds lasting relationships by prioritizing transparency and trust, making her a valued partner to both clients and colleagues.

Tonya Brown has her bachelor’s degree in business administration and is a licensed life and health agent. She has been an Account Manager for 15 years and is the day-to-day contact for your employee benefit program. She focuses on putting people first and is known for her consistent, and quality client support.

Sheri Smith is a licensed Life and Health Insurance Agent who brings over 15 years of experience in employee benefits and account management. Sheri is known for her proactive problem-solving, attention to detail, and ability to foster strong client relationships. Her people-first mindset and approachable demeanor help clients feel supported and understood—making her a reliable resource in small-group benefits management and a steady force within The Enterprise Team.

Maria Olandez holds an Associate of Arts degree and is a licensed Life and Health Insurance Agent with 5 years of industry experience. She focuses on the daily management of small-group benefits, emphasizing education and client service. Maria is dedicated to helping clients understand the importance of insurance coverage while providing dependable, high-touch support throughout the process.

Alicia Sanders is a licensed Life and Health Insurance Agent with a Bachelor of Science degree and a strong background in client engagement, business development, and marketing strategy. As Director of Sales and New Business Marketing, Alicia guides prospective clients through the complex landscape of employee benefits while cultivating brand presence and growth opportunities. Her collaborative approach across departments helps ensure consistent service delivery and clear communication, empowering clients to make well-informed benefits decisions.

Carole Singleton brings over 20 years of experience in insurance and employee benefits, combining financial leadership with operational oversight. As CFO, Carole ensures accuracy and compliance across accounting, payroll, licensing, and core HR functions. Her disciplined approach supports financial integrity and fosters the smooth operation of the agency. A valued member of the leadership team, Carole champions both fiscal responsibility and a people-centered workplace culture.

Raene Chambers-Henry holds a Bachelor’s degree in Business Administration from the University of Central Florida and brings over 15 years of experience as a licensed Life and Health Insurance Agent. In her role as Director of Account Management, Raene leads with strategic insight, aligning team strengths to deliver meaningful value to both employers and employees. Her expertise spans large-group benefits administration, technology integration, and full-cycle client support. Raene’s leadership ensures efficient, personalized solutions that help clients navigate benefits with confidence and ease.

Terry Singleton has more than 25 years of experience in employee benefits consulting and has consulted for some of the largest and smallest business in the US. Terry is the CEO and Managing Partner of The Enterprise Team. He is also an equity partner in United Benefit Advisor, the 10th largest employee benefit advisory organization in the world. Terry is the founder of United Benefit Advisors of Florida, LLC and he holds active health, life, annuities and general lines licenses in Florida, and many other states.