Caroline D. Ciraolo recently spoke with Bloomberg Tax Editor at Large Rebecca Baker for Bloomberg’s Talking Tax podcast. Caroline and Rebecca discussed the flood of tax professionals entering the private sector in the wake of the Trump administration’s push to reduce the federal workforce.
Caroline discussed an initiative within the tax bar that connects individuals whose federal employment offers were rescinded by the IRS or the Justice Department’s Tax Division in January 2025, and now, current and recently departed federal tax professionals with law firms and other private employers. As she noted during the podcast, Caroline understands the challenges of transitioning from government to private sector work, given she served as Acting Assistant Attorney of the Tax Division at the Justice Department from 2015 to 2017 before returning to private practice.
In particular, Caroline talked about key transferable skills developed in public service that many in the private sector will find valuable, including the extensive training provided by the government, the attention to detail, advocacy, and writing skills, and a love for the practice area.
“That passion for unpacking complicated transactions and complicated facts and circumstances, identifying the issues—those skills are equal on both sides,” she said.
Listen to the full podcast here.
About Caroline
Caroline is a former Acting Assistant Attorney General of the U.S. Department of Justice’s Tax Division and a founder of Kostelanetz’s Washington, D.C. office. Her practice focuses on federal and state civil tax controversies, including representation in sensitive audits, administrative appeals, and litigation, providing tax advice, conducting internal investigations, and representing individuals and entities in criminal tax investigations and prosecutions. She also serves as a consulting and testifying expert witness, as well as an independent mediator in tax disputes.
