Our Team - The Enterprise Team

TERRY SINGLETON

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.

Stephanie Samuels

Stephanie Samuels brings over 15 years of experience in employee benefits, operations, and leadership. As Chief Operating Officer of The Enterprise Team, she oversees internal processes, team development, and service delivery to ensure operational excellence and consistent client outcomes. Her work supports strategic alignment across departments and enhances both client and employee experience.

With a Bachelor of Science in Economics and Psychology and a Life and Health Insurance License, Stephanie combines analytical insight with industry expertise to lead with precision and purpose. Her background includes benefits administration, compliance oversight, and organizational design. She is skilled in guiding high-performing teams, streamlining workflows, and implementing scalable systems that support long-term growth. Her thoughtful leadership and hands-on approach make her a trusted partner in both internal operations and client-facing strategy.

CAROLE SINGLETON

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

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.

Alexa Guglielmi

Alexa Guglielmi is The Enterprise Team’s Director of Communications & Engagement and Executive Assistant to CEO Terry Singleton. She leads the team’s communications, social media, and client engagement initiatives while coordinating events and supporting executive operations.

With a focus on creativity, precision, and connection, Alexa helps strengthen The Enterprise Team’s brand, culture, and relationships across clients, partners, and the community. Guided by her “work hard, play hard” philosophy, she brings energy, professionalism, and purpose to everything she does.

ALICIA SANDERS

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.

LYNNE MAHN

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.

Carmen Camacho

Carmen Camacho is a Licensed Insurance Agent with 20 years of experience in the Employee Benefits and client relationship management.

She specializes in helping employers navigate complex benefits strategies while delivering exceptional service and finding solutions to support employee engagement and retention.

Carmen is passionate about building trusted relationships, and consistently exceeding client expectations. She is passionate about account management and is committed to customer success and helping employers make informed decisions while educating employees become better consumers

Sheri Bell

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.

Leslie McDonald

Leslie McDonald has her Bachelor of Arts degree from California State University, Fullerton.

As an HR Technology Specialist she has built and managed Employee Navigator portals for the last eight years for several UBA Brokers. She implements technology and tools to help clients manage employee benefits, making their daily HR tasks easier.

Jessica Sista

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.

Actuarial Analysis

Are you better off with a fully insured plan or a self funded plan?

Leverage the power of data to make informed decisions. Our actuarial system analyzes complex datasets to provide you with actionable insights, helping you optimize risk assessment and cost projections.

How competitive are your benefits?

Our advanced statistical methodologies and cutting-edge tools reveal hidden opportunities, allowing you to make strategic choices that set you apart from the competition. Directly compare the benefits you offer to what your competitors are offering.

Are your solutions designed with you and your team in mind?

No matter your needs, we’ve got you covered. From pension plans to health insurance, our adaptable solutions are designed to meet your specific requirements, ensuring maximum value and efficiency for your business.

SHANNA DRISCOLL

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.

HR CONSULTING SERVICES

How do you keep up with HR trends, news and benefits administration information?

Keeping track of regulations and benefits trends and ensuring your company remains compliant can be difficult, costly and time-consuming. Never miss a beat with our benchmark information, news on legislation changes and open enrollment information. Our up-to-date documents will save you time and keep you in the loop.

Are your employees getting the most out of your benefits program?

Tackle your mounting employee communication concerns with customizable benefits announcements, employee newsletters and presentations.

Is your employee handbook up to date?

Failing to keep an employee handbook updated is consistently one of the top mistakes employers make with their handbooks. Let us help you make sure your handbook is updated to properly reflect legislation and organization changes.

COMMUNICATION SERVICES

Are you up to date on relevant news and legislation?

We make it easy for you by distributing monthly and quarterly benefits newsletters that explain changes in legislation and how those changes affect your organization.

Do you have small or understaffed HR departments?

We have benchmarking and benefits administration information that can provide much-needed HR support and assistance.

How often do you hear from your current broker?

Open enrollment won’t be the only time you hear from us. We’ll email you regularly to keep in touch and let you know we’re here to help.

COMPLIANCE SERVICES

Are you compliant with all federal benefits laws, rules and regulations?

There are countless rules and regulations governing employee benefit plans, many of which are complex. Our resources will help you meet your compliance obligations and keep you up to date on laws and regulations that affect your employee benefits program.

Do you have access to constantly updated compliance bulletins and guides?

Our easy-to-read articles will help you find answers to your common COBRA, FMLA, health care reform, HIPAA, Medicare Part D and Section 125 questions.

Do you want to know about benefit changes at a glance?

Our monthly and quarterly newsletters provide concise, attorney-reviewed summaries of benefits rule changes to keep you up to date with the latest regulations.

BENEFIT ADVISORY

Are you up to date on relevant news and employee benefits legislation?

We make it easy for you by distributing benefits newsletters that explain changes in legislation and how those changes affect your organization.

How often do you hear from your current broker?

Open enrollment won’t be the only time you hear from us. We’ll email you regularly and provide you with monthly newsletters and timely industry updates to keep in touch and let you know we’re here to help.

Are your employees getting the most out of your benefits program?

An attractive benefits package won’t help you retain employees if your employees aren’t aware of your benefits offerings. Our agency can deliver the resources—including informational articles, videos and infographics—you need to effectively communicate with your employees about benefits offerings and enrollment.

BENEFIT ADMINISTRATION

Are you up to date on federal, state and local benefits laws, rules and regulations?

There are countless rules and regulations governing employee benefit plans, many of which are complex. Our resources will help you meet your compliance obligations and keep you up to date on laws and regulations that affect your employee benefits program.

Do you have A small or understaffed HR department?

HR departments are often short on time and swamped with numerous important tasks. Let us help you manage your benefits administration tasks with our easy-to-use resources.

Do your employees realize the true value of the benefits you provide?

Employees are more likely to appreciate their benefits packages if they truly understand all that is provided to them. We can help you give employees a visual that shows the portion of their total compensation that is employee benefits.

ISAAC EBURY

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.

TONYA BROWN

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

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

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.

Monday	9:00 AM – 5:00 PM
Tuesday	9:00 AM – 5:00 PM
Wednesday	9:00 AM – 5:00 PM
Thursday	9:00 AM – 5:00 PM
Friday	9:00 AM – 5:00 PM
Saturday	Closed
Sunday	Closed

Our Altamonte Team

Partnered with United Benefit Advisors of Florida

Partner Office Leaders