About Us

Chesapeake Benefits is a locally owned, independent health and life insurance brokerage firm serving Mid-Atlantic businesses and individuals since 1987.

Who We Are

We Are Health Benefits

Chesapeake Benefits clients range in size from self-employer groups to groups with five hundred lives. In addition, we sell and service many personal plans to local residents. Our staff takes great pride in their abilities to provide insurance solutions and claims services.

Years in the Business

Happy Clients

Carriers We Work With

Our Story

First and foremost, Chesapeake Benefit Services strives to maintain the highest level of professional and ethical standards.

As an independent brokerage firm, we are not committed to any one product or vendor. Our recommendations are based solely on the needs of the customer and what makes sense for them.

We represent a broad line of product. We offer a wide assortment of high-quality products from a broad range of vendors. In addition to conventional insurance products, Chesapeake Benefit Services markets a number of unique product offerings. These include group and individual medical, high deductible major medical for individuals, and short-term medical for non-COBRA individuals.

We believe that each customer is unique. We are independent in our judgment and comprehensive in our approach to customer solutions. We understand that different customers will have different needs.

Chesapeake Benefits is staffed to handle all phases of new business development and implementation. However, we believe the real value of our partnership begins after the sale. We maintain customer support every step of the way to serve as their advocates for all of their benefit plans.

Our customers can expect to communicate with us in a new and more efficient ways by means of enhanced technology.

Contact Our Team

Our Team of Experts

Lori Kern

President, Group Consultant and Senior Broker


With over 30 years of experience working with employee benefits, Lori brings a level of expertise that incorporates all facets of a benefit consultant. With knowledge and work experience from an employer, carrier and broker perspective, Lori is able to develop and preserve client relationships to the highest degree.

Meryl A. Kern

Meryl A. Kern

Executive Account Manager

Voted top 100 Brokers in Maryland by the Maryland Health Connection and over ten years experience in health insurance, Meryl provides excellent services to her group, individual, and medicare clients. Meryl specializes in small and large group employee benefits and works with employers to find plans that both benefit the employee and employer. Additionally, Meryl takes pride in helping her clients navigate individual and Medicare supplemental markets. She exemplifies what it means to be a leader and works diligently to advocate for her clients needs.
Michelle Christopher

Michelle Christopher

Medicare & Individual Specialist

With over 23 years of experience in human resources and employee
benefits, Michelle provides knowledge and understanding in claims
resolution and benefit implementation. Michelle is AHIP certified and specializes in all Medicare aspects. Michelle Works directly with her clients
providing assistance with choosing a Health, Part D, Dental and Vision plan which best suits their needs and budget. Medicare can be confusing,
Michelle helps Beneficiaries understand what is available to them.
Anna Sissom

Anna Sissom

Account Manager

Anna joined our team in 2019 as an Administrative Assistant, and is now the Account Manager. She specializes in navigating the Maryland Health Connection as well as working directly with carriers. Anna works diligently with Employers, Individuals and Medicare clients to choose the right insurance that best meet their needs. She strives to provide excellent customer service and maintains a level of professionalism
with each and every client.

“Chesapeake Benefits has been a joy to work with. Our business requires that we have medical, dental and life insurance. Chesapeake Benefits has come through with flying colors on all. The ‘drop everything let me take care of it’ client attitude is what they have given us whenever we have needed anything. Her quick response is matched by none. If you want an agent who makes you feel like you are her only client then I recommend Lori from Chesapeake Benefit Services.”

Rachel DeAngelis

Chief Financial Officer, Davis Dealership

“I have very complex and difficult personal insurance needs. I place a premium on ease, simplicity and straight communication. That’s why I’m so pleased with  Chesapeake Benefits. They placed everything I was looking for in a prompt and responsive manner.”

Mr. Herbert Ford

Farmer, Chesapeake Benefits Customer

“Chesapeake Benefit Services has always worked hard to ensure that our family support agency is properly covered so we can maintain our day-to-day arts activities. Greg Dawson is always just a call away for our small nonprofit. When our coverage needs changed, Chesapeake Benefits did the legwork so that we were properly insured, without missing a beat.”

Linda Sawson

Executive Committee Member, Kent Forward

Join Us

Our Clients Are Like Family

The core of our business philosophy is to view our clients and customers as partners. We strive to work with our partners to find and design benefit solutions that will improve their bottom line by lowering overhead cost. We aim to enhance their ability to recruit and retain quality employees by providing high-value, high-quality benefit programs.

Contact Us

Please feel free to contact us any time. We are prepared to answer questions about our benefits plans, help with claims or simply planning for the future. Whatever the case, we are at your service.

860 Washington Ave. Chestertown, MD 21620

M-F: 8am-5pm, S-S: Closed

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