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Chesapeake Health Benefits
Average rating:  
 5 reviews
 by Monica Fuchs
Very knowledgeable

Anna was very helpful and very knowledgeable!

 by Michele Moore
Anna rocks!

Anna Sissom made setting up my health insurance in retirement easy and affordable! Her knowledge of the different plans and responsiveness to my questions were key to me completing the daunting task of navigating and choosing which plan was best for me. Thanks Anna!!

 by Carolyn Burton
Gratitude

I have had the true pleasure to work with Anna Sissom for the past 2+ years through a variety of health plan changes for myself and my family. Having spent 28 years in human resources -- many of those as a plan administrator for group health insurance plans for employees -- I know the ins and outs of benefits and of great customer service. Anna excels at both! She helped me navigate the change from an employer plan to a plan on the exchange in the fall of 2022 with such ease and helped us find affordable options. When we had an unexpected health emergency shortly afterwards, she was right there to help us navigate the insurance snafu I inadvertently created. We've been on and off group and marketplace health and dental plans these past few years as jobs have changed, and each time we need to make a change, Anna is there with her smiling voice, her deep knowledge and her seemingly-effortless patience.

I chose your office based on prior customer feedback -- customers who had been former employees in a group plan I administered -- and I am so glad I did!

I am so grateful for Anna and for the services Chesapeake Benefits offer in our local community!

 by Debra Bittner
Gratitude

Two years ago, I retired at age 56 to take care of my aging parents. Navigating the health care system for benefits was overwhelming. Somehow, I got connected with Anna Sissom, what a great connection!!!! I haven’t had too many issues/questions, but when I do, I have direct access to someone who is on top of her game.
• Anna speaks clearly. She listens. Asks appropriate questions.
• She seems interested in my circumstances rather than trying to fit me into a ‘mold’.
• Anna clearly knows her work. She knows the health care portal. She understands the billing, the tax credits, the process.
• Anna gives the impression that she genuinely cares that my issues are resolved.

 by Kate Wilber
Extremely Helpful!

I needed help getting a new health insurance policy set up for me in Maryland because I recently moved from another state. I contacted Meryl at Chesapeake Health Benefits and she advised me on the best options and helped me get everything set up. She was extremely helpful and made the process quick and easy!

We Are Always Here to Help

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.

Ongoing Support

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.

Contact Us

Appointments are required to ensure dedicated 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-4pm, S-S: Closed

Summer Hours: Memorial Day-Labor Day: Monday-Thursday 8am-4pm, F-Sun: Closed

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