Cindy Whaley

Cindy Whaley


Avery Hall Benefit Solutions
410-822-7300 ext: 1101
408 N Washington St Suite A, Easton, MD 21601

Cindy Whaley is the president of Avery Hall Benefit Solutions, Inc. and is based in Easton. She joined Avery Hall as vice president of Benefit Solutions and opened the Easton office in 1994 with only three employees. She became president shortly after the benefit solutions teams in Easton and Salisbury combined into one collective company in 2009. Her focus is sales, administration, and management of all areas of benefit solutions. She specializes in employee benefits for businesses as well as helping employers figure out a cost-effective approach to offering their staff the best benefits within budget.

Cindy is a past recipient of the Caroline County Chamber of Commerce Business Woman of the Year award. She has been honored multiple times as a Golden Eagle Award recipient by the National Association of Health Underwriters (NAHU) in recognition of her personal sales production. Additionally, she was the club secretary for Soroptimist of Talbot County (SITC) and previously served as a SITC club director as well as a delegate. Cindy has also served as both the treasurer and secretary for the Eastern Shore Association of Health Underwriters and as a past president and membership chair of the Chesapeake Chapter for the National Association of Insurance and Financial Advisors. She served as treasurer and vice president for the Choptank Community Health Systems Board of Directors; secretary for Caroline County Library Board of Directors; and participated as a fundraising committee member for Habitat for Humanity Choptank.

Prior to Avery Hall, Cindy worked in sales and product development with CareFirst BlueCross BlueShield, Delmarva Health Plan, and Sovran Bank.

Cindy was born in Milwaukee, WI and raised in West Chester, PA. She lived in Richmond, VA for 10 years before moving to Federalsburg, MD in 1988. Cindy attended the University of Richmond on a partial basketball scholarship where she also received her Bachelor of Science in business administration with a double major in marketing and management from the E. Claiborne Robins School of Business.

Cindy currently resides in Denton, MD with her husband Dave. They have two grown sons who live and work in Salisbury, MD. In her free time, she enjoys going to the beach, quilting, reading, and completing Sudoku puzzles.