
About Us
Dennis Insurance Group is a family-owned employee benefits advisory firm in Greensboro, North Carolina with its beginning dating back to 1954. We tailor insurance options to meet the expectations of our clients and their employees. Our dedicated team of Benefits Advisors and Account Managers bring significant experience to each area of your employee benefit plans. We feel there is great strength and take pride in always doing what is right and being responsive to every situation. As our clients will attest, when it comes to your business, we are a trusted source, focusing on making your business better and making sure your number one asset, your employees, come back the next day.
Lenwood Dennis, Founder, remains active in daily activities and all accounts of the firm. Danielle Dennis Grady, President, joined the firm in 1990 and is a Benefits Advisor as well as manages the day-to-day operations of the firm. Herbert W. Oliver, Jr., Vice President, is Lenwood’s son-in-law and joined the firm in 1997 and is a Benefits Advisor. We believe the difference in our firm is in how we work together to bring our best to you now and in the future.
We are committed to:
- Being the most educated benefit advisory firm an employer can choose in the marketplace.
- Delivering your benefit administration staff and your employees an experience like never before benefit administration.
- Effectively managing your benefit expenditures through innovative advice and proven administration solutions.
- Enhancing employee communication and benefit plan perception with high-tech services.
- Improving your benefit administration through integrated benefit technology.

Benefits Delivered
Employee Benefits
The employees are a company’s greatest asset. Keeping up with the latest in benefit offerings and value added services may be a daunting task, but the Dennis Insurance Group team is here to help. We take an innovative approach so that your business offers superior benefit solutions to attract and retain the top talent in your industry. We make a great effort to ensure your company meets its employees’ needs and desires in a cost-effective manner to maximize performance and profitability.
- Small and Large Group Medical
- Fully Insured
- Level-Funded
- Self-Funded
- Life and Disability Insurance
- Dental
- Vision
- Health Reimbursement Arrangements (HRA)
- Health Savings Account (HSA)
- ICHRA and Flexible Spending Account (FSA)
Retirement Plans
Retirement Plans are an excellent addition to your employee benefits package. A Dennis Insurance Group Investment Advisory Representative will provide advice and guidance to formulate a plan that meets your objectives. Through our partnership with industry leading record keepers, we are pleased to offer comprehensive services for qualified retirement plans.
- Profit Sharing/401k
- Defined Benefit Pension
- IRA
- SIMPLE IRA
- SEP IRA
Executive / Individual Benefits and Planning
Executive and Individual benefits are designed to provide business owners, key employees and individuals with high level benefits and financial protection for their companies, their families and themselves. These benefits can help attract and reward top people in an organization as well as bridge the retirement income gap.
- Individual Medical
- Medicare Strategies
- Individual Life Insurance
- Long Term Care Plans
- Buy Sell / Business Continuation
- Disability buy-out
- Disability Income Protection
- Key Person
- Executive Medical Reimbursement Plans
- Estate Planning
- Deferred Compensation
Benefits Delivered
Employee Benefits
Your people are your greatest asset. Keeping up with the latest in benefit offerings and added value services may be a daunting task, but the Dennis Insurance Group team is here to help. We take an innovative approach so that your business offers superior benefit solutions to attract and retain the top talent in your industry. We are making a great effort to ensure your company meets its employees’ needs and desires in a cost-effective manner to maximize performance and profitability.
- Small and Large Group Medical
- Fully Insured
- Level-Funded
- Self-Funded
- Life and Disability Insurance
- Dental
- Vision
- Health Reimbursement Arrangements (HRA)
- Health Savings Account (HSA)
Retirement Plans
Retirement Plans are an excellent addition to your employee benefits package. A Dennis Insurance Group Investment Advisory Representative will provide advice and guidance to formulate a plan that meets your objectives. Through our partnership with industry leading record keepers, we are pleased to offer comprehensive services for qualified retirement plans.
- Profit Sharing/401k
- Defined Benefit Pension
- IRA
- 412-I Plan, 419 (e)
- Keogh
- SIMPLE IRA
- SEP IRA
Executive / Individual Benefits and Planning
All too often the important needs of the individual are ignored by industry. We understand how hard it is to figure all this out on your own.
Each person is unique. We carefully listen to what you share and then develop the correct plan that will fit your specific circumstances.
Once your plan is effective, you continue to have access to our help and expertise. Whether it is a problem with a claim, or obtaining medication or medical care, we are there ready to assist. Choosing the right insurance for you and your family is an important decision. We understand, and we want you to feel confident in your choice.
Executive benefits are designed to provide business owners and key employees with high level benefits and financial protection. These benefits are powerful tools to help attract and reward top people in your organization and bridge the retirement income gap.
For business owners with a company to run you know how difficult it is to get away. What happens if you or your business partner becomes disabled? How would cash flow, revenues and profitability be affected? Executive benefit plans help lay the groundwork to ensure business continuity if you or another owner can no longer maintain ownership.
- Individual Medical
- Medicare Strategies
- Individual Life Insurance
- Long Term Care Plans
- Buy and Sell
- Disability buy-out and disability income for the owners
- Key Person
- Executive Medical Reimbursement Plans
- Estate Planning
- E.S.O.P.
- Deferred Compensation

HR Delivered
We are here to assist with your HR task, from HR questions and guidance to communication and enrollment of benefits. Whether you are a full-time HR professional, or HR is just one of the many responsibilities that you have, we have the tools and services that make your HR task easier. We offer customized enrollment forms, employee orientations, employee meetings and online employee portals. We will assist in enrolling your employees with online enrollment systems or tried and true paper forms.
HR Delivered
We are here to assist with your HR tasks, from HR questions and guidance to communication and enrollment of benefits. Whether you are a full-time HR professional, or HR is just one of the many responsibilities that you have, we have the tools and services that make your HR tasks easier.
We offer customized enrollment forms, employee orientations, employee meetings and online employee portals. We will assist in enrolling your employees with online enrollment systems or tried and true paper forms.

Compliance Delivered

Keeping track of the multitude of Federal and State regulations can be complicated. We will assist you in evaluating your compliance with COBRA and ERISA. We can also help establish processes to maintain compliance. As new rules are promulgated, we will provide updates and explanations of the new requirements.
The ACA introduced new challenges to HR compliance. Dennis Insurance Group will review your compliance with the ACA. We can put in place strategies that will limit your exposure under the law and assist with the required reporting.
Dennis Insurance Group will host a platform that provides on-demand answers to complicated HR and benefit questions. This service includes training courses and a process for creating employee handbooks.

Benchmark Survey
Since 2005, United Benefit Advisors® (UBA) has surveyed employers nationwide to create the definitive employee benefits database. This valued data is used to create an annual report highlighting national employer-sponsored health plan trends by region, state, industry, and size. In addition, this year’s report includes various non-medical employee benefits to reflect employers enhancing their benefit programs. The 2024 survey represents $13+ billion in healthcare dollars spent, nearly 1,000,000 employees, and 7,800+ employers nationwide.
As a UBA Partner Firm, we have digital access to the entire survey database in real-time. Cost, funding methods, enrollment, plan design, coverage features, wellness, and prescription drug coverage are available for analysis.
Employers can reliably benchmark their plans against their region, industry, and size. Each year, we provide our clients with top trends in the market

Download a free copy of the latest UBA Survey and Benchmarking report:
Click Here to read the 2024 UBA Health Survey Executive Summary.
Click Here to read the 2024 North Carolina Health Plan Trends
To obtain a survey report for another region, or a customized comparison of your benefits plans, request a consultation below

United Benefit Advisors® (UBA) is the nation’s leading independent employee benefits advisory organization with more than 200 offices throughout the United States, Canada, and Europe. UBA empowers 2,000+ advisors to maintain independence while capitalizing on each other’s shared knowledge and market presence to provide best-in-class services and solutions.
UBA Partner Firms are benefit advisors who understand the unique needs of their local community. While remaining independent, they join together to gain knowledge and resources from other UBA Partner Firms across the country. As a result, UBA Partner Firms offer sophisticated, cost-effective solutions equal to or better than those from large brokerages while continuing to provide the personal service that only an independent, local advisor can deliver.
- Ranked top 10 in benefits revenue for 10+ years
- Serving more than 36,000 employers
- Over 2,000 employee benefit professionals
- National and local leverage and buying power