Pat Schneider:

Kelly Ruppel grew up on a dairy farm outside Racine, headed to the west coast for college and worked in Washington D.C. before moving back to the Midwest and becoming a private consultant to the embattled Chicago Public Schools system.
When she received a job offer from new Madison Schools Superintendent Jennifer Cheatham, whom she met when Cheatham was a top administrator at Chicago Public Schools, she and her husband packed their bags.
Today Ruppel is Cheatham’s chief of staff, one of five top administrators hired by Cheatham with ties to Chicago since taking the reins of the Madison School District in April.
In addition to Ruppel, a former principal at Civic Consulting Alliance, they include:
Alex Fralin, assistant superintendent for secondary schools and former Deputy Chief of Schools for CPS
Rodney Thomas, special assistant to the superintendent and former director of Professional Development and Design for the Chicago Board of Education
Nancy Hanks, deputy assistant superintendent for Elementary Schools and a former Chicago public elementary school principal
Jessica Hankey, director of strategic partnerships and innovation, formerly manager of school partnerships at The Field Museum in Chicago.

Fascinating. Are these new positions, or are the entrants replacing others? 10/2013 Madison School District organization chart (PDF).
Related: “The thing about Madison that’s kind of exciting is there’s plenty of work to do and plenty of resources with which to do it,” Mitchell said. “It’s kind of a sweet spot for Jen. Whether she stays will depend on how committed the district is to continuing the work she does.”