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Thomas Cryan, Jr., Ivins, Phillips & Barker, Chartered Photo

Thomas M. Cryan, Jr.


Clients love Tom’s ability to respond quickly and efficiently with practical advice on complex and unique issues.  When he's not advising clients, he's a proud dad watching his son play college football and his daughter play college rugby and perform in music theater.


Tom's practice is focused on executive compensation, fringe benefits, and employment tax matters. He advises clients on tax audits, as well as drafting and amending fringe benefit policies and compensation plans. He also assists clients with structuring compensation arrangements to comply with Section 409A of the Internal Revenue Code. He is experienced in the application of Section 3121 (FICA), the deduction rules under Section 274, and the Golden Parachute provisions in Section 280G. In addition, he has assisted clients with the federal and state tax implications of mobile workforces.

Tom's experience also encompasses employee benefits 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 the application of the new Employee Retention Credit. He has also represented clients before the IRS and U.S. Department of the Treasury in connection with policy issues.

Tom works closely with clients' tax, benefits, and legal departments to resolve complex issues related to payroll and information reporting, executive compensation, and employment tax issues in a practical and cost-effective manner.

Tom is an accomplished public speaker and regularly presents at professional organizations such as the Tax Executives Institute, American Bar Association, and the American Benefits Council. Tom also co-authored the Tax Management Portfolio on Golden Parachutes.


Georgetown University Law Center, LL.M., 1999

George Mason University School of Law, magna cum laude, 1997

Washington & Lee University, cum laude, 1994

Bar & Court Admissions

District of Columbia


United States Tax Court


The Honorable Joel Gerber, United States Tax Court

Memberships & Affiliations

Member, Bloomberg BNA Compensation Planning Journal advisory board

Honors & Awards

Best Lawyers in America, 2022

Bloomberg BNA Certificate of Excellence – Golden Parachutes Portfolio


Representative Matters

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 a highly mobile workforce in designing internal procedures for the proper taxation of travel reimbursements and per diem payments.

Represented a Fortune 100 company in a meeting with the 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 an on-site employer cafeteria and the tax treatment of conferences and conventions.

Assisted a large financial institution with internal restructuring in order to avoid 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 multi-state employer to defend a state income tax audit regarding the withholding of non-resident wage income.

Obtained more than a dozen Section 162(m) private letter rulings (PLRs) across the past ten years.

Worked with an an acquisition target company to analyze potential Section 280G implications of compensation plans and employment agreements.

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