Alderman Shiller has a long history of bringing creative job training programs to the ward. In 1998 and through 2003, Alderman Shiller joined with South Side community activist Eddie Reed and Truman College to create a very successful construction and trades apprenticeship program that resulted in dozens of community members learning important trade and construction skills.

In 2006, Alderman Shiller worked with the Mayor's Office of Workforce Development, Truman College, the Organization of the Northeast, Truman College and Dawson Technical Institute to create a one-of-a-kind program where TIF funds from Wilson Yard go to training area residents in the trades. By wedding the use of TIF funds and a new city bid incentive ordinance,  area residents who successfully complete the Dawson Technical Institute program will be eligible to work on the Wilson Yard construction project.

Alderman Shiller has also brought a Mayor's Office of Workforce Development outpost to the ward. And, the ward service office stays in contact with hundreds of employers in order to maintain an extensive directory of job openings for area residents.