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Meet Our Staff

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

Principal Agent

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.

Cindy-Riddleberger

Cindy Riddleberger

Agency Representative

Cindy is the agency representative for Riddleberger Insurance Agency. She has more than 30 years of experience in the insurance industry, selling commercial, farmowners, automobile, home and life insurance.

She is the second generation of her family to work in the agency, which was founded in 1959.

Cindy is an Elite certified Farm Insurance Agent for Nationwide’s Agribusiness Company, the highest designation for agents selling farm insurance products with Nationwide.

She was named the Businesswoman of the Year award by the Caroline County Chamber of Commerce in 2016.

Jennifer-Paesch

Jennifer Paesch

Agency Manager

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.

She lives in Ridgely with her husband Fred and enjoys spending time with her growing family!

Brenda-Wroten

Brenda Wroten

Associate Agent

Brenda is an associate agent for Riddleberger Insurance Agency in the Denton office. She has been in insurance since 1991 and is licensed in property and casualty and life and health insurance.

She specializes in personal insurance coverage such as auto, home, recreational, umbrella and life.

Brenda is a lifelong resident of the Eastern Shore and resides in Ridgely with her husband Michael, daughters Sienna and Sadie, and fur babies Brody and Prue.

Julie-Burack

Julie Burack

Associate Agent

Julie is an associate agent with Riddleberger Insurance Agency in the Denton office and has been with the agency since 2016.

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.

Anna Smith

Property/Casualty Licensed Agent

Anna is a licensed agent with Riddleberger Insurance Agency in the Chestertown office. She has more than 40 years in customer service, with 20 years as a property/casualty licensed agent.

Anna is involved in the community through her church outreach programs. She likes to garden, read, crochet and travel.

Terri-Smith

Terri Smith

Associate Agent

Terri is an associate agent with Riddleberger Insurance Agency in the Chestertown office. She has been in the insurance industry for over 20 years, writing personal as well as agribusiness and commercial policies.

She likes to spend time with her family and her dog, do needlework, garden, and take long drives in her Mustang with the top down.

cynthia-a-rifenburg

Cynthia A Rifenburg

Associate Agent

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.

Shannon-O'Neill

Shannon O'Neill

Associate Agent

Shannon is an associate agent with Riddleberger Insurance Agency in the Chestertown office. She has worked at the agency since 2016. She has her property and casualty license as well as life and health insurance license.

She has an associate degree in business administration and brings her passion to help educate clients in making smart choices.

When she’s not in the office, you can find her on the hiking trails with her fur child, Autumn.

Aaron-Schmitt

Aaron Schmitt

Farm / Commercial Agent

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.

Michele Davis

Associate Agent

Michele is an associate agent with Riddleberger Insurance Agency in the Denton office. She can assist you with all your account and billing needs.

Michele moved to Caroline County when she was 16. She has been active within the community starting as a teenager volunteering at the Goldsboro Fire Company, to Elementary PTA, volunteering at His Hope Haven Homeless Shelter, and Church Missions including Raceway Ministries.

Starting her career working 15 years with the Postal Service until downsizing caused her position to be eliminated. She then moved to the medical field. Due to the stress COVID put on the medical field and with other factors, she decided to make a change in career fields and was recommended to Riddleberger Insurance. Now that she is licensed to do personal lines (home, auto, & recreational vehicles), she looks forward to helping people with their insurance needs.

Michele resides in Goldsboro with her husband, Tim. She has 2 children, Shelby and Tad, and 2 grandchildren, Breanna and Raelynn. She attends Greensboro Baptist Church. In her spare time, she enjoys her time with her family (including her fur babies), horseback riding, home improvements, and vacations.

Lisa-Taylor

Lisa Taylor

Customer Service Representative

Lisa has 30 years’ experience in office administration and customer service. At Riddleberger Insurance Agency in the Chestertown office, she handles all the billing inquiries and payments.

Lisa enjoys crabbing, a good movie and spending time with her grandchildren.

Nathan Harding

Associate Agent

Nathan is an associate agent with Riddleberger Insurance Agency in the Chestertown office. He has been in the insurance industry since 2020, specializing in Commercial, Personal and Life insurance.
Nathan has his bachelor’s in economics from Lycoming college with a minor in accounting.

Born and raised in Dorchester County, currently lives in Talbot County. His hobbies include golfing, hiking, boating, and snowboarding.