Cindy Winckler was born in Des Moines, Iowa. She moved to Davenport when she was young, and has continued to be a part of the Davenport community throughout her adult years. Public service has been a part of her family background. Her dad owned the snack bar at the Scott County Courthouse, through an agreement with the county and the disabled veterans' organization. Her mother was a long-time deputy city clerk and city alderman and mayor pro tem.

She is a graduate of West High School in Davenport. She earned a BSE in Home Economics from Northeast Missouri State University and her master's degree in Educational Technology from the University of Northern Iowa. Cindy has been a family and consumer science teacher in small and large school districts in Iowa - Davis County, Pleasant Valley, Calamus and Davenport. She retired as a Quality Learning Consultant with the Mississippi Bend Area Education Agency in Bettendorf and continues her work on education equity issues. In her capacity as a Quality Learning Consultant, she worked with teachers, administrators and school districts to plan and implement student achievement initiatives. Cindy was named to Who's Who Among America's Teachers in February 2000.

Cindy and her husband, Joe, were married in 1973. They have two adult children, Joseph Bradley and Courtney Elizabeth. Her son, Joe, his wife Jennifer, and sons Alex and Jack reside in Lee's Summit, Missouri. Courtney and her husband Jeff and their children EJ, Haley, Meghan and Samuel reside in Bloomington, Illinois.

Cindy is currently serving as a commissioner on the Education Commission of the States. She is a member of the Davenport Schools Network for Community and School Partnerships.