Our Team

A professional agency with personal service.

Crawford Yingling Insurance is a Carroll County, Maryland independent insurance agency with experienced professionals.  We take pride in our expertise and professional development, currently all of our representatives either hold or are working towards an accredited insurance designation. We specialize in marketing and placing commercial and personal insurance in Maryland, Virginia, and Pennsylvania.  Our goal is to educate our clients and advocate on their behalf.  Our promise to our clients is WHEN SOMETHINGS HAPPENS, WE WILL BE THERE.  The Crawford Yingling Insurance team includes:

John B. Yingling, A.A.I.

President, CFO


john headshotAfter graduating from Towson University in 1971 and having worked in the financial services industry, John joined Crawford-Cash Inc. in 1976. In 1983 he became president of Crawford Yingling Insurance. In 1995 he earned the Accredited Advisory of Insurance designation (A.A.I.). John is past president of the Carroll County Association of Independent Insurance Agents, serving on the board of the Independent Insurance Agents of Maryland, Inc. He is currently the treasurer of the Greater Westminster Development Corporation, serves on the Board of Carroll Hospital Center and is a board member for The Carroll Community College Foundation. John specializes in business, automobile and homeowners accounts.

Benjamin Yingling, CIC, CRM, CLCS, CRIS®

Vice President


ben headshotBenjamin serves as Vice President of the agency and oversees all aspects of the business. Ben strives to help businesses implement and leverage risk management strategies to better position themselves in the insurance marketplace. He recently obtained the Certified Insurance Counselor Designation and Certified Risk Manager Designation after completing over 200 hours of course work and multiple comprehensive essay examinations. In additional he holds the Commercial Lines Coverage Specialist Designation, Construction Risk Insurance Specialist Designation, Ben is the current Chairman of the Board for the Carroll County Chamber Of Commerce, and sits on The Maryland Chamber of Commerce board of directors. He is a board governor for the Loyola Blakefield Alumni Association and is past chairman of the Carroll Hospital Golf Committee. Ben is also an active Rotarian. Ben resides in Westminster, MD with his wife Amy.

Jennifer Trimble, ACSR

Account Executive


jennifer headshot

Jennifer joined Crawford Yingling Insurance in 2013 after serving multiple roles in the mortgage industry.  Jennifer specializes in servicing business and personal lines accounts. In 2015 Jennifer obtained the Accredited Customers Service Representative Designation, a highly respected and sought after accolade in the industry.  Jennifer’s effective communication and expertise has garnered her high praise from clients and her peers.  Jennifer holds an Associates Degree in Business Management from Frederick Community College and resides in Frederick, MD with her husband Mark.