Jay co-founded the software start-up company, Cartegraph Systems in 1994. Cartegraph started in the basement of a home and grew into a nationally recognized company, providing software and service to local governments across the United States and providing local employment to over 100 professionals. Jay is currently the Executive Director of the NICC-StartUp Dubuque program through the Iowa Small Business Development Center in Dubuque.
Jay was appointed to the supervisor position in March 2016 and re-elected in the 2016 General Election, receiving over 33,000 votes. Starting in January 2017, Jay was elected to serve as the chairperson of the Dubuque County Board of Supervisors and was reelected as Chair in 2018.