Charles Chieppo launched Chieppo Strategies LLC in 2006 after more than a decade shaping and writing about Massachusetts public policy issues. He is also a senior fellow at Pioneer Institute, a Massachusetts public policy think tank. From 2019-22, he taught public policy writing at Suffolk University.

Chieppo has appeared regularly on WGBH television’s Greater Boston, WGBH’s Boston Public Radio and WBUR’s RadioBoston. For several years, Chieppo's columns appeared regularly in The Boston Herald. Other publications in which his work has been featured include The Wall Street Journal, The Boston Globe, National Review, Governing, Education Next, USA TODAY, Washington Times, Providence Journal, Nashville Tennessean and CommonWealth.

From 2003 to 2005, Chieppo served as policy director in Massachusetts’ Executive Office for Administration and Finance, where he led the Romney administration's successful effort to reform the commonwealth's public construction laws, helped develop and enact a new charter school funding formula, and worked on a variety of public employee labor issues such as pension reform and easing state restrictions against privatization.

Previously, he directed the Shamie Center for Better Government at Pioneer Institute. While employed by Pioneer, Chieppo served on the MBTA's Blue Ribbon Committee on Forward Funding and has written and commented extensively on T and other transportation issues. He was a contributor to "MBTA Capital Spending Derailed by Expansion," by the Massachusetts Taxpayers Foundation with Pioneer Institute, which won the Government Research Association's "Most Distinguished Research" award.

Chieppo is a graduate of Boston University's College of Communication and Vanderbilt University Law School.