Tax Rep Network with Eric Green

To DOJ Tax and Back Again: A Sit-down With Caroline Ciraolo

Tax Rep Network with Eric Green

Show Notes

Kostelanetz Partner and Former Acting Assistant Attorney General for the Tax Division, Caroline Ciraolo, joins Eric Green for an insightful conversation about one of the most fascinating careers in tax controversy. Caroline shares her journey from Tax Court clerk to private practice, leading the Department of Justice Tax Division, and returning to one of the nation's premier tax controversy firms. They discuss what really happens inside DOJ, the professionalism of government attorneys, why relationships matter in the tax community, and how volunteering and getting involved can transform your career. They also explore why today's enforcement environment presents one of the greatest opportunities in years for attorneys, CPAs, and Enrolled Agents looking to build or expand a tax controversy practice. Whether you're just entering IRS representation or already handling complex cases, this episode is packed with practical career advice, leadership lessons, and behind-the-scenes insights from one of the most respected voices in tax controversy.

In this episode you'll learn: • What it's really like leading the DOJ Tax Division • Common misconceptions about government tax attorneys • Why networking and professional organizations accelerate your career • How to build a successful tax controversy practice • Why today's IRS enforcement environment creates tremendous opportunity

Be sure to subscribe—Part 2 with Caroline will focus exclusively on how to build and scale a thriving tax controversy practice.

Want to contact Caroline? She can be found here: https://kostelanetz.com/our-people/caroline-d-ciraolo

More from Tax Rep Network with Eric Green

Oct 22, 2026

Your clients trust you with their taxes—but who is asking them the questions that could protect their family, their business, and their financial future?

Oct 19, 2026

What if the biggest thing holding back your tax or accounting practice is the way you’ve always gotten new clients?

Oct 16, 2026

What if the key to growing your tax or accounting firm isn’t working harder or hiring more people—but eliminating the work you shouldn’t be doing in the first place?

Oct 14, 2026

More than 11 million taxpayers have been identified as non-filers—and for tax professionals, that represents a massive opportunity to solve serious problems, deliver tremendous value, and build a highly profitable representation practice.

Sep 30, 2026

The IRS has fewer employees. Artificial intelligence is taking on a bigger role. Enforcement is becoming more targeted. And the way cases are selected, worked—and appealed—may be about to change dramatically.

See all episodes →