Thomas M. Cryan, Jr. concentrates his practice on various tax matters, including:

  • Executive compensation
  • Fringe benefits
  • Employment tax areas

He counsels clients regarding tax audits as well as drafting and amending fringe benefit policies and compensation plans. Tom also assists clients in structuring compensation arrangements to comply with Section 162(m) of the Internal Revenue Code (IRC). He has experience in the application of Code section 3121 (FICA), the deduction rules under Code Section 274 and the Golden Parachute provisions under Code section 280G.

Tom’s experience encompasses employee benefits and information reporting, in particular, dealing with the income and employment tax treatment of settlement payments, use of corporate aircraft, statutory fringe benefits, nonqualified deferred compensation, travel benefits, wellness programs and employer obligations under the Affordable Care Act. In addition, he has assisted clients with the state tax implications of mobile workforces. Tom has also represented clients before the IRS and the U.S. Department of Treasury in connection with policy initiatives.

Tom is positioned to work closely with employers to resolve complex payroll and information reporting issues. He works with employer’s tax, benefits, payroll and legal departments to resolve executive compensation and employment tax issues in the most practical and cost effective manner. 

Tom’s successes related to benefits include:

  • Assisted a large biotechnology company in the application of the IRS rules impacting spousal travel, the personal use of corporate aircraft, mixed business-personal flights and the recently revised deduction disallowance rules for the entertainment use of corporate aircraft
  • Assisted an employer with highly mobile workforce in designing internal procedures for the proper taxation of travel reimbursements and per diem payments
  • Represented a Fortune 100 company at a meeting with the U.S. Department of the Treasury regarding the taxation of wellness programs
  • Represented a Fortune 100 company at IRS appeals on the tax treatment of relocation reimbursements and use of corporate aircraft. IRS conceded the issues in full
  • Represented an employer on the taxation of on-site employer cafeteria and the tax treatment of conferences and conventions

Due to his knowledge of employment taxes, he has:

  • Assisted a large financial institution in internal restructuring in order to avoid the FICA restart provisions, and therefore reduce the company's out-of-pocket employment tax costs while addressing the company's concerns regarding its internal payroll tax administration
  • Represented a large manufacturing company in protesting a large employment tax deposit penalty. Penalty was abated at IRS Appeals
  • Worked with a large multistate employer in defending a state income tax audit on the withholding of nonresident wage income

He has achieved the following regarding executive compensation:

  • Obtained more than a dozen Section 162(m) private letter ruling (PLRs) over the last 10 years
  • Worked with target company in analyzing potential Section 280G implications of compensation plans and employment agreements

Tom is an accomplished public speaker and regularly presents at professional organizations such as the Tax Executive Institute, American Bar Association and American Benefits Council.

Professional & Community Affiliations


Bloomberg BNA Compensation Planning Journal Advisory Board


Omicron Delta Epsilon National Economics Honor Society

Washington and Lee University

News, Analysis & Press

Important Labor & Employment Provisions Included in Federal Tax Bill

Ohio Chamber of Commerce Blog

December 28, 2017

Rex Tillerson May Make Unusual Tax Argument

Wall Street Journal

January 11, 2017

Silicon Valley Cafeterias Whet Appetite of IRS

Wall Street Journal

September 2, 2014

News Analysis: What's at Stake in Quality Stores

Tax Analysts

September 3, 2013

Silicon Valley's Mouthwatering Tax Break

Wall Street Journal

April 7, 2013

Sixth Circuit Affirms Quality Stores Decision on FICA Taxation of Severance Pay - Billions of Dollars in Refund Claims are at Issue

Bloomberg BNA

October 1, 2012

Books & Book Chapters

  • Golden Parachutes, Tax Management Portfolio No. 396 - 2nd edition, Co-author, 2015

Speaking Engagements

Avoiding Employee and Fringe Benefit Landmines

Tysons Corner, VA

December 13, 2018

Tackling Taxing Challenges in 2018: The Telework/Mobile Work Phenomenon and Tax Reform

Littler Executive Employer, Phoenix, AZ

May 3, 2018
2017 Florida Employer Conference

Miami, FL

October 17, 2017
Tax Treatment of Popular Fringe Benefits

Tysons Corner, VA

October 11, 2017

Immigration Compliance Updates Under the Trump Administration

2017 Mid-Atlantic Employer Conference, Washington, D.C.

June 6, 2017

Segment on IRS's New Priority to Crack Down on Employer-Provided Meals

Fox News - In the News

September 4, 2014


  • LL.M. in Taxation, Georgetown University Law Center, 1999
  • J.D., George Mason University School of Law, 1997magna cum laude
  • B.A., Washington and Lee University, 1994cum laude

Bar Admission

District of Columbia


  • U.S. Tax Court