As our client, you will have a team of highly qualified professionals working for you to provide you with the best coverage for you, your family, or your business. Building a long-lasting relationship with our clients is our number one priority.
Matt Riddleberger
Matt Riddleberger is a third generation insurance agent who joined the family business, Riddleberger Insurance Agency, in 2009.
Matt is a Caroline County native and is proud of our tight-knit community. He still lives in Denton with his wife, Nicole, and two kids, Camryn and Gabriel. He enjoys the Eastern Shore lifestyle of hunting, fishing and boating with his family.
Matt holds insurance licenses in Maryland, Delaware, Virginia and Pennsylvania and can help serve all your insurance needs.
Jennifer Paesch
Jennifer is the agency manager and has been with Riddleberger Insurance Agency since 2017. She has been licensed in property/casualty and life/health insurance since 2003 and works with clients on their personal, commercial and agribusiness needs. She also handles whole and term life insurance, fixed annuities.
She is licensed in MD, DE, and VA and is a Notary Public for the State of Maryland.
She lives in Ridgely with her husband Fred and enjoys spending time with her growing family!
Aaron Schmitt
Aaron is an associate agent with Riddleberger Insurance Agency in the Chestertown office. He has been in the insurance industry since 2019, specializing in Farm and Commercial Insurance.
He has his Bachelor’s in Economics from West Virginia University. He is a Farm Certified agent and been working in the agricultural sector for over 15 years.
Aaron resides in Denton, MD and has two daughters, Jillian and Sailor. He enjoys spending time with family and friends and playing golf.
Julie Burack
Julie is an associate agent with Riddleberger Insurance Agency in the Denton office and has been with the agency since 2006.
She sells property, auto, commercial, farm and life insurance, and recently completed an Agribusiness Farm Certification class.
A Greensboro native, she now lives in Ridgely with her husband of 32 years, David. She has three children, Natalie Burack Bilbrough, Carolina Burack Peter, and Joseph Burack.
Julie attends Greensboro Pentecostal Church, and she likes flower gardening, baking, family history and spending time with family and friends.
Cynthia A Rifenburg
Cindy has been an associate agent with Riddleberger Insurance Agency in the Denton office since 2019. She has been in the Insurance Industry and licensed in property/casualty and life/health insurance in Maryland & Delaware since 1990.
She sells and services property, auto, recreational vehicles, umbrella, commercial, farm and life insurance. She specializes in commercial insurance.
Cindy was born and raised in Caroline County, and now resides in Bridgeville, DE.
She is an active member of the Federalsburg Lions Club, and in her free time enjoys gardening, vacationing in the tropics, and spending time with her family and friends.
Sara Thompson
Sara is an Associate Agent with Riddleberger Insurance in the Chestertown office. She holds a Property & Casualty and Life and Health License.
Sara is a new resident of Maryland. She was born and raised in Bucks County, PA. She has a strong background in medical, dental, and mental health billing, she has been in the healthcare industry for 20 years.
Sara lives in Betterton, MD, with her husband, son, daughter, and their dog, Ellie.
She enjoys spending time with her family and friends here in MD and PA, and enjoys boating on the Chesapeake Bay.
Carly Shuhart
Carly is an Associate Agent with Riddleberger Insurance in our Denton office. After six years in the banking industry, Carly transitioned into insurance to follow her passion for helping people protect what matters most. She has been licensed in Property, Casualty, and Life insurance for two years and takes pride in guiding clients through their coverage options with care and clarity. Carly loves living in Caroline County, MD, and spends her free time with her twin daughters, Riley and Carter.
Shelby Joseph
Shelby is an Associate Agent with Riddleberger Insurance in our Denton office.
Newly licensed in property and casualty insurance, she is committed to delivering top-notch service and support to her clients. Making sure their needs are met with care and professionalism.
She is from the small town of Laurel, Delaware. In her spare time, she loves being outside and spending time with her husband, Robert III, and their son, Robert IV.
Debbi Darling
Debbi is an Associate Agent with Riddleberger Insurance in our Denton office. Debbi has been in the insurance industry for over 22 years, licensed in Maryland and Delaware.
Born and raised in Caroline County, she lives with her husband, Alton, in Denton. She has three children, Alton, Paige, and Madison, and a granddaughter, Aurora.
Debbi enjoys hiking in the mountains, boating/fishing on the Choptank River, and kayaking with her husband.
Cassidy Cummings
Cassidy is an associate agent at Riddleberger Insurance in the Chestertown office.
She is a newly licensed Property & Casualty Insurance Agent in Maryland and looks forward to helping clients to the best of her ability. She was raised on the Eastern Shore and now lives in Kent County. Outside of work, Cassidy enjoys spending time with her family and her two dogs, Daisy and Beau.
